Di- and polyazides. Synthesis, chemical transformations and practical applications

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Abstract

The chemistry of organic di- and polyazides has been extensively developed in recent years. Methods for the synthesis of 1,1- and 1,2-diazides are diverse and include stoichiometric, catalytic, photochemical and electrochemical approaches. These organic compounds are highly reactive and are involved in a wide range of reactions, from thermal transformations to click chemistry. Of particular attention are transformations, in which one azido group undergoes intramolecular cyclization, while another azido group remains intact and can participate in further chemical transformations. Tri- and polyazides are investigated as precursors for the production of high-energy materials and the synthesis of high-molecular-weight compounds. This review addresses the methods for the synthesis of organic compounds containing two or more azido groups and their chemical transformations. Aliphatic, aromatic and heteroaromatic diazides are considered. Specific transformations characteristic of geminal and vicinal diazides, which differ from the reactions of monoazides, are described. Examples of the practical application of di-, tri- and polyazides are highlighted. The bibliography includes 355 references

About the authors

Biligma Dashievna Tsyrenova

Lomonosov Moscow State University, Faculty of Chemistry

Candidate of chemical sciences

Pavel Sergeevich Lemport

Lomonosov Moscow State University, Faculty of Chemistry

Candidate of chemical sciences, Researcher

Valentin Georgievich Nenajdenko

Lomonosov Moscow State University, Faculty of Chemistry

Email: nen@acylium.chem.msu.ru
ORCID iD: 0000-0001-9162-5169
Scopus Author ID: 35495423300
ResearcherId: R-2277-2016
Doctor of chemical sciences, Professor

References

  1. E.V.Scriven, K.Turnbull. Chem. Rev., 88, 297 (1988)
  2. G.L'abbe. Chem. Rev., 69, 345 (1969)
  3. T.Curtius. Ber. Dtsch. Chem. Ges., 23, 3023 (1890)
  4. T.Curtius, K.Heidenreich. Ber. Dtsch. Chem. Ges., 27, 2684 (1894)
  5. P.A.S.Smith. Org. React., 3, 337 (1946)
  6. J.H.Boyer, F.C.Canter. Chem. Rev., 54, 1 (1954)
  7. G.Wypych. Handbook of Foaming and Blowing Agents. (1st Edn.) (Toronto: ChemTec Publishing, 2017)
  8. T.-S.Lin, W.H.Prusoff. J. Med. Chem., 21, 109 (1978)
  9. E.Saxon. Science, 287, 2007 (2000)
  10. H.Staudinger, J.Meyer. Helv. Chim. Acta, 2, 635 (1919)
  11. C.W.Tornce, C.Christensen, M.Meldal. J. Org. Chem., 67, 3057 (2002)
  12. V.V.Rostovtsev, L.G.Green, V.V.Fokin, K.B.Sharpless. Angew. Chem., Int. Ed., 41, 2596 (2002)
  13. H.N.Handivada, X.Jiang, J.Lahann. Adv. Mater., 19, 2197 (2007)
  14. A.H.El-Sagheer, T.Brown. Acc. Chem. Res., 45, 1258 (2012)
  15. T.Kakuta, T.Yamagishi, T.Ogoshi. Chem. Commun., 53, 5250 (2017)
  16. W.Yu, L.Jiang, C.Shen, P.Zhang. Drug Dev. Res., 77, 319 (2016)
  17. P.M.E.Gramlich, C.T.Wirges, A.Manetto, T.Carell. Angew. Chem., Int. Ed., 47, 8350 (2008)
  18. Organic Azides: Syntheses and Applications. (Eds S.Brase, K.Banert). (Wiley, 2009)
  19. I.E.Celik, S.F.Kirsch. Eur. J. Org. Chem., 53 (2021)
  20. A.P.Haring, S.F.Kirsch. Molecules, 20, 20042 (2015)
  21. K.Bensberg, S.F.Kirsch. Synthesis, 54, 4447 (2022)
  22. V.A.Bakulev, Y.M.Shafran, N.A.Beliaev, T.V.Beryozkina, N.N.Volkova, M.N.Joy, Z.Fan. Russ. Chem. Rev., 91, RCR5042 (2022)
  23. K.Banert. Synthesis, 48, 2361 (2016)
  24. M.Meldal, C.W.Tornce. Chem. Rev., 108, 2952 (2008)
  25. M.O.Forster, H.E.Fierz, W.P.Joshua. J. Chem. Soc., Trans., 93, 1070 (1908)
  26. M.B.Sohn, M.Jones, M.E.Hendrick, R.R.Rando, W.V.E.Doerin. Tetrahedron Lett., 13, 53 (1972)
  27. Y.Takeuchi, K.Takagi, T.Yamaba, M.Nabetani, T.Koizumi. J. Fluorine Chem., 68, 149 (1994)
  28. V.A.Zapol'skii, J.C.Namyslo, M.Gjikaj, D.E.Kaufmann. Synlett, 1507 (2007)
  29. M.O.Forster, R.Muller. J. Chem. Soc., Trans., 97, 126 (1910)
  30. G.Landen, H.W.Moore. Tetrahedron Lett., 17, 2513 (1976)
  31. E.-S.A.M.Badawey, S.M.Rida, F.S.G.Soliman, T.Kappe. Monatsh. Chem., 120, 1159 (1989)
  32. E.Malle, W.Stadlbauer, G.Ostermann, B.Hofmann, H.J.Leis, G.M.Kostner. Eur. J. Med. Chem., 25, 137 (1990)
  33. C.O.Kappe. Liebigs Ann. Chem., 5, 505 (1990)
  34. E.E.Gilbert. J. Energ. Mater., 5, 77 (1987)
  35. R.E.Conrow, W.D.Dean. Org. Process Res. Dev., 12, 1285 (2008)
  36. A.Hassner, M.Stern, H.E.Gottlieb, F.Frolow. J. Org. Chem., 55, 2304 (1990)
  37. R.A.A.U.Ranaweera, J.Sankaranarayanan, L.Casey, B.S.Ault, A.D.Gudmundsdottir. J. Org. Chem., 76, 8177 (2011)
  38. D.A.Evans, T.C.Britton, J.A.Ellman, R.L.Dorow. J. Am. Chem. Soc., 112, 4011 (1990)
  39. S.Kirchmeyer, A.Mertens, G.A.Olah. Synthesis, 500 (1983)
  40. K.Nishiyama, A.Watanabe. Chem. Lett., 13, 455 (1984)
  41. K.Nishiyama, T.Yamaguchi. Synthesis, 106 (1988)
  42. H.Suzuki, C.Nakaya. Synthesis, 641 (1992)
  43. K.Nishiyama, M.Oba, A.Watanabe. Tetrahedron, 43, 693 (1987)
  44. C.Ye, H.Gao, J.A.Boatz, G.W.Drake, B.Twamley, J.M.Shreeve. Angew. Chem., Int. Ed., 45, 7262 (2006)
  45. H.Suzuki, Y.S.Hwang, C.Nakaya, Y.Matano. Synthesis, 1218 (1993)
  46. H.Bretschneider, N.Karpitschka. Monatsh. Chem., 84, 1091 (1953)
  47. K.M.Moriarty, J.M.Kliegman, C.Shovlin. J. Am. Chem. Soc., 89, 5958 (1967)
  48. R.M.Moriarty, B.R.Bailey, I.Prakash, R.S.Miller. J. Org. Chem., 50, 3710 (1985)
  49. M.J.O'Hare, D.Swern. Tetrahedron Lett., 14, 1607 (1973)
  50. C.-G.Shin, Y.Yonezawa, K.Suzuki, J.Yoshimura. Bull. Chem. Soc. Jpn., 51, 2614 (1978)
  51. A.Hassner, J.Keogh. J. Org. Chem., 51, 2767 (1986)
  52. D.A.Kamble, P.U.Karabal, P.V.Chouthaiwale, A.Sudalai. Tetrahedron Lett., 53, 4195 (2012)
  53. P.Klahn, H.Erhardt, A.Kotthaus, S.F.Kirsch. Angew. Chem., Int. Ed., 53, 7913 (2014)
  54. N.Okamoto, T.Sueda, H.Minami, Y.Miwa, R.Yanada. Org. Lett., 17, 1336 (2015)
  55. T.Harschneck, S.Hummel, S.F.Kirsch, P.Klahn. Chem.-Eur. J., 18, 1187 (2012)
  56. M.Uyanik, N.Sahara, M.Tsukahara, Y.Hattori, K.Ishihara. Angew. Chem., Int. Ed., 59, 17110 (2020)
  57. A.Bredenkamp, F.Mohr, S.F.Kirsch. Synthesis, 47, 1937 (2015)
  58. H.Erhardt, A.P.Haring, A.Kotthaus, M.Roggel, M.L.Tong, P.Biallas, M.Jubermann, F.Mohr, S.F.Kirsch. J. Org. Chem., 80, 12460 (2015)
  59. K.Holzschneider, A.P.Haring, S.F.Kirsch. Eur. J. Org. Chem., 2824 (2019)
  60. A.Hassner. Acc. Chem. Res., 4, 9 (1971)
  61. H.Ohta, M.J.Yoshida. Synth. Org. Chem., Jpn., 28, 453 (1970)
  62. A.Hassner, R.J.Isbister, A.Friederang. Tetrahedron Lett., 10, 2939 (1969)
  63. C.Chen, J.Gea, L.He. Org. Chem. Front., 9, 2116 (2022)
  64. G.Schroeter. Ber. Dtsch. Chem. Ges., 42, 2336 (1909)
  65. S.Gotzky. Chem. Ges. A/B, 64, 1555 (1931)
  66. H.Lindemann, A.Muhlhaus. Justus Liebigs Ann. Chem., 446, 1 (1926)
  67. S.J.Danishefsky, M.P.DeNinno, S.H.Chen. J. Am. Chem. Soc., 110, 3929 (1988)
  68. W.Zhou, L.Zhang, N.Jiao. Angew. Chem., Int. Ed., 48, 7094 (2009)
  69. M.Sandberg, L.K.Sydnes. Tetrahedron Lett., 39, 6361 (1998)
  70. M.Yokoyama, S.Hirano, M.Matsushita, T.Hachiya, N.Kobayashi, M.Kubo, H.Togo, H.Seki. J. Chem. Soc., Perkin Trans. 1, 13, 1747 (1995)
  71. M.C.Pirrung, F.Blume. J. Org. Chem., 64, 3642 (1999)
  72. T.Kappe, G.Lang, E.Pongratz. J. Chem. Soc., Chem. Commun., 338 (1984)
  73. K.Holzschneider, M.L.Tong, F.Mohr, S.F.Kirsch. Chem.-Eur. J., 25, 11725 (2019)
  74. W.Ogilvie, W.Rank. Can. J. Chem., 65, 166 (1987)
  75. H.Erhardt, F.Mohr, S.F.Kirsch. Eur. J. Org. Chem., 5629 (2016)
  76. H.Erhardt, K.A.Kunz, S.F.Kirsch. Org. Lett., 19, 178 (2017)
  77. F.Ballaschk, H.Erhardt, S.F.Kirsch. RSC Adv., 7, 55594 (2017)
  78. G.-X.Dong, J.-S.Li, T.-H.Chan. J. Chem. Soc., Chem. Commun., 1725 (1995)
  79. L.Barash, E.Wasserman, W.A.Yager. J. Am. Chem. Soc., 89, 3931 (1967)
  80. A.G.Harter, T.M.Klapotke, C.Riedelsheimer, J.Stierstorfer, M.Voggenreiter. Eur. J. Inorg. Chem., 2241 (2021)
  81. P.P.Samuel, S.Kundu, C.Mohapatra, A.George, S.De, P.Parameswaran, H.W.Roesky. Eur. J. Org. Chem., 2327 (2017)
  82. S.Arepally, V.N.Babu, A.Polu, D.S.Sharada. Eur. J. Org. Chem., 5700 (2018)
  83. F.Borghi, I.E.Celik, P.Biallas, F.Mittendorf, S.F.Kirsch. Eur. J. Org. Chem., 4389 (2020)
  84. P.Biallas, S.F. Kirsch. Tetrahedron Lett., 58, 4209 (2017)
  85. N.F.Albertson, B.F.Tullar, J.A.King, B.B.Fishburn, S.Archer. J. Am. Chem. Soc., 70, 1150 (1948)
  86. J.A.Castro-Osma, A.Lara-Sanchez, A.Otero, A.M.Rodriguez, M.C.de la Torre, M.A.Sierra. Eur. J. Org. Chem., 682 (2016)
  87. P.Biallas, J.Heider, S.F.Kirsch. Polym. Chem., 10, 60 (2019)
  88. P.Biallas, T.M.Mensak, K.A.Kunz, S.F.Kirsch. J. Org. Chem., 84, 1654 (2019)
  89. H.Erhardt, F.Mohr, S.F.Kirsch. Chem. Commun., 52, 545 (2016)
  90. P.Biallas, A.P.Haring, S.F.Kirsch. Org. Biomol. Chem., 15, 3184 (2017)
  91. A.P.Haring, P.Biallas, S.F.Kirsch. Eur. J. Org. Chem., 1526 (2017)
  92. R.Carrie, D.Danion, E.Ackermann, R.W.Saalfrank. Angew. Chem., Int. Ed. Engl., 21, 287 (1982)
  93. R.Carrie, D.Danion, E.Ackermann, R.W.Saalfrank. Angew. Chem., Suppl., 21 (S4), 660 (1982)
  94. H.K.Hall, M.Ramezanian, F.D.Saeva. Tetrahedron Lett., 29, 1235 (1988)
  95. R.W.Saalfrank, U.Wirth. Chem. Ber., 122, 519 (1989)
  96. P.S.Lemport, I.V.Smolyar, V.N.Khrustalev, V.A.Roznyatovsky, A.V.Popov, V.A.Kobelevskaya, I.B.Rozentsveig, V.G.Nenajdenko. Org. Chem. Front., 6, 335 (2019)
  97. A.V.Shastin, B.D.Tsyrenova, P.G.Sergeev, V.A.Roznyatovsky, I.V.Smolyar, V.N.Khrustalev, V.G.Nenajdenko. Org. Lett., 20, 7803 (2018)
  98. R.W.Saalfrank, H.Maid. Chem. Commun., 5953 (2005)
  99. R.Galli, V.Malatesta. Org. Prep. Proced. Int., 3, 231 (1971)
  100. G.Emmer, E.Zbiral, G.Brill, H.Musso. Liebigs Ann. Chem., 6, 796 (1979)
  101. A.Kirschning. Eur. J. Org. Chem., 2267 (1998)
  102. R.Carrie, D.Danion, E.Ackermann, R.W.Saalfrank. Angew. Chem., Int. Ed. Engl., 21, 288 (1982)
  103. R.Carrie, D.Danion, E.Ackermann, R.W.Saalfrank. Angew. Chem. Suppl., 21 (S4), 668 (1982)
  104. R.W.Saalfrank, U.Wirth. Chem. Ber., 122, 969 (1989)
  105. R.W.Saalfrank, E.Ackermann, M.Fischer, U.Wirth, H.Zimmermann. Chem. Ber., 123, 115 (1990)
  106. R.W.Saalfrank, C.-J.Lurz, J.Hassa, D.Danion, L.Toupet. Chem. Ber., 124, 595 (1991)
  107. M.Ramezanian, A.B.Padias, F.D.Saeva, H.K.Hall. J. Org. Chem., 55, 1768 (1990)
  108. R.W.Saalfrank, U.Wirth, C.-J.Lurz. J. Org. Chem., 54, 4356 (1989)
  109. R.W.Saalfrank, M.Fischer, U.Wirth, H.Zimmermann. Angew. Chem., Int. Ed. Engl., 26, 1160 (1987)
  110. B.D.Tsyrenova, V.G.Nenajdenko. Molecules, 25, 480 (2020)
  111. B.D.Tsyrenova, V.N.Khrustalev, V.G.Nenajdenko. J. Org. Chem., 85, 7024 (2020)
  112. B.D.Tsyrenova, V.N.Khrustalev, V.G.Nenajdenko. Org. Biomol. Chem., 19, 8140 (2021)
  113. P.Portius, P.W.Fowler, H.Adams, T.Z.Todorova. Inorg. Chem., 47, 12004 (2008)
  114. X.Q.Zeng, W.G.Wang, F.Y.Liu, M.F.Ge, Z.Sun, D.X.Wang. Eur. J. Inorg. Chem., 416 (2006)
  115. M.Goebel, K.Karaghiosoff, T.M.Klapotke. Angew. Chem., Int. Ed., 118, 6183 (2006)
  116. R.Haiges, J.A.Boatz, A.Vij, V.Vij, M.Gerken, S.Schneider, T.Schroer, M.Yousufuddin, K.O. Christe. Angew. Chem., Int. Ed., 43, 6676 (2004)
  117. T.M.Klapotke, B.Krumm, M.Scherr, R.Haiges, K.O.Christe. Angew. Chem., Int. Ed., 46, 8686 (2007)
  118. T.M.Klapotke, B.Krumm, M.Scherr. Inorg. Chem., 47, 4712 (2008)
  119. R.Haiges, J.A.Boatz, A.Vij, M.Gerken, S.Schneider, T.Schroer, K.O.Christe. Angew. Chem., Int. Ed., 42, 5847 (2003)
  120. T.M.Klapotke, B.Krumm, K.Polborn. J. Am. Chem. Soc., 126, 710 (2004)
  121. T.M.Klapotke, B.Krumm, P.Mayer, I.Schwab. Angew. Chem., Int. Ed., 42, 5843 (2003)
  122. T.M.Klapotke, B.Krumm, P.Mayer, H.Piotrowski, O.P.Ruscitti, A.Schiller. Inorg. Chem., 41, 1184 (2002)
  123. L.E.Chapman, R.F.Robbins. Chem. Ind., 29, 1266 (1966)
  124. T.Curtius, A.Bertho. Ber. Dtsch. Chem. Ges. B, 59, 565 (1926)
  125. W.Kesting. Ber. Dtsch. Chem. Ges. B, 57, 1321 (1924)
  126. K.Banert, Y.-H.Joo, T.Rueffer, B.Walfort, H.Lang. Angew. Chem., Int. Ed., 46, 1168 (2007)
  127. X.Zeng, M.Gerken, H.Beckers, H.Willner. Inorg. Chem., 49, 9694 (2010)
  128. A.M.Nolan, B.K.Amberger, B.J.Esselman, V.S.Thimmakondu, J.F.Stanton, R.C.Woods, R.J.McMahon. Inorg. Chem., 51, 9846 (2012)
  129. M.G.Darzens. C.R.Hebd. Seances Acad. Sci., 154, 1232 (1912)
  130. C.V.Hart. J. Am. Chem. Soc., 50, 1922 (1928)
  131. E.Ott, H.Weissenburger. Ber. Dtsch. Chem. Ges. B, 70, 1829 (1937)
  132. F.D.Marsh. J. Org. Chem., 37, 2966 (1972)
  133. W.P.Norris, R.A.Henry. J. Org. Chem., 29, 650 (1964)
  134. D.Lucet, T.L.Gall, C.Mioskowski. Angew. Chem., Int. Ed., 37, 2580 (1998)
  135. M.S.Mortensen, G.A.O'Doherty. Chemtracts: Org. Chem., 18, 555 (2005)
  136. F.Betzler, T.Klapoetke, S.Sproll. Eur. J. Org. Chem., 509 (2013)
  137. S.Kasina, A.R.Fritzberg, D.L.Johnson, D.Eshima. J. Med. Chem., 29, 1933 (1986)
  138. R.Pajkert, T.Bottcher, M.Ponomarenko, M.Bremer, G.-V.Roschenthaler. Tetrahedron, 69, 8943 (2013)
  139. M.Swetha, P.V.Ramana, S.G.Shirodkar. Org. Prep. Proced. Int., 43, 348 (2011)
  140. S.C.Zimmerman, K.D.Cramer, A.A.Galan. J. Org. Chem., 54, 1256 (1989)
  141. Y.Inaba, T.Fujimoto, H.Ono, M.Obata, S.Yano, Y.Mikata. Carbohydr. Res., 343, 941 (2008)
  142. S.Saito, H.Yokoyama, T.Ishikawa, N.Niwa, T.Moriwake. Tetrahedron Lett., 32, 663 (1991)
  143. T.S.Zatsepin, E.A.Romanova, D.A.Stetsenko, M.J.Gait, T.S.Oretskaya. Nucleosides, Nucleotides Nucleic Acids, 22, 1383 (2003)
  144. F.A.El-Essawy. Nucleosides, Nucleotides Nucleic Acids, 24, 1265 (2005)
  145. H.Naka, N.Kanase, M.Ueno, Y.Kondo. Chem.-Eur. J., 14, 5267 (2008)
  146. D.Pini, A.Iuliano, C.Rosini, P.Salvadori. Synthesis, 1023 (1990)
  147. A.Pordea, D.Mathis, T.R.Ward. J. Organomet. Chem., 694, 930 (2009)
  148. D.R.Reddy, E.R.Thornton. J. Chem. Soc., Chem. Commun., 23, 172 (1992)
  149. C.M.Marson, R.C.Melling. Synthesis, 247 (2006)
  150. A.Hui, J.Zhang, Z.Wang. Synth. Commun., 38, 2374 (2008)
  151. A.Blum, J.Bottcher, A.Heine, G.Klebe, W.E.Diederich. J. Med. Chem., 51, 2078 (2008)
  152. T.Kano, Y.Hato, A.Yamamoto, K.Maruoka. Tetrahedron, 64, 1197 (2008)
  153. M.J.Gresser, P.A.Keller, S.M.Wales. Tetrahedron Lett., 50, 4899 (2009)
  154. J.Skarzewski, A.Gupta. Tetrahedron: Asymmetry, 8, 1861 (1997)
  155. A.J.Brouwer, H.J.van der Linden, R.M.J.Liskamp. J. Org. Chem., 65, 1750 (2000)
  156. B.K.Majeti, P.P.Karmali, B.S.Reddy. J. Med. Chem., 48, 3784 (2005)
  157. H.Loibner, E.Zbiral. Helv. Chim. Acta, 59, 2100 (1976)
  158. C.Cere, F.Peri, S.Pollicino, A.Ricci. ChemInform, 30 (2010)
  159. A.Arcelli, V.Cere, F.Peri, S.Pollicino, A.Ricci. Tetrahedron, 57, 3439 (2001)
  160. J.McNulty, R.Mo, A.Capretta, C.S.Frampton. Chem. Commun., 2384 (2001)
  161. A.Scheurer, P.Mosset, R.W.Saalfrank. Tetrahedron: Asymmetry, 8, 1243 (1997)
  162. V.N.Azev, M.D'Alarcao. J. Org. Chem., 69, 4839 (2004)
  163. P.Guedat, B.Spiess, G.Schlewer. Tetrahedron Lett., 35, 7375 (1994)
  164. M.V.De Almeida, R.M.Figueiredo, H.F.Dos Santos, A.D.Da Silva, W.B.De Almeida. Tetrahedron Lett., 42, 2767 (2001)
  165. S.G.Gouin, J.-F.Gestin, K.Joly, A.Loussouarn, A.Reliquet, J.C.Meslin, D.Deniaud. Tetrahedron, 58, 1131 (2002)
  166. C.E.Song, J.W.Yang, E.J.Roh, S.Lee, J.H.Ahn, H.Han. Angew. Chem., Int. Ed., 41, 3852 (2002)
  167. A.-G.Amr, K.A.Ali, M.M.Abdalla. Eur. J. Med. Chem., 44, 901 (2009)
  168. A.Franconetti, E.Alvarez, F.Cabrera-Escribano. Synlett, 28, 201 (2017)
  169. M.Gottschaldt, D.Koth, H.Gorls. Org. Biomol. Chem., 3, 1170 (2005)
  170. S.Tejera, R.L.Dorta, J.T.Vazquez. Tetrahedron: Asymmetry, 27, 896 (2016)
  171. F.Minisci, R.Galli. Tetrahedron Lett., 3, 533 (1962)
  172. G.V.A.Lenardon, L.Nicchio, M.Fagnoni. J. Photochem. Photobiol. C, 46, 100387 (2021)
  173. E.Zbiral, K.Kischa. Tetrahedron Lett., 10, 1167 (1969)
  174. W.E.Fristad, T.A.Brandvold, J.R.Peterson, S.R.Thompson. J. Org. Chem., 50, 3647 (1985)
  175. T.Suzuki, A.Shibata, N.Morohashi, Y.Ohba. Chem. Lett., 34, 1476 (2005)
  176. B.B.Snider, H.Lin. Synth. Commun., 28, 1913 (1998)
  177. F.D.Tropper, F.O.Andersson, S.Braun, R.Roy. Synthesis, 618 (1992)
  178. T.Inazu, K.Kobayashi. Synlett, 869 (1993)
  179. R.M.Moriarti, J.S.Khosrowshahi. Tetrahedron Lett., 27, 2809 (1986)
  180. P.Magnus, M.B.Roe, C.Hulme. J. Chem. Soc., Chem. Commun., 263 (1995)
  181. M.Arimoto, H.Yamaguchi, E.Fujita, Y.Nagao, M.Ochiai. Chem. Pharm. Bull., 37, 3221 (1989)
  182. T.Sasaki, K.Kanematsu, Y.Yukimoto. J. Org. Chem., 37, 890 (1972)
  183. R.Chung, E.Yu, C.D.Incarvito, D.J.Austin. Org. Lett., 6, 3881 (2004)
  184. S.Nocquet-Thibault, A.Rayar, P.Retailleau, K.Cariou, R.H.Dodd. Chem.-Eur. J., 21, 14205 (2015)
  185. A.Chennaiah, S.Bhowmick, Y.Vankar. RSC Adv., 7, 41755 (2017)
  186. J.Liu, Z.Fang, X.Liu, Y.Doua, J.Jiang, F.Zhang, J.Qu, Q.Zhu. Chin. Chem. Lett., 31, 1332 (2020)
  187. G.Fumagalli, P.T.G.Rabet, S.Boyd, M.F.Greaney. Angew. Chem., Int. Ed., 54, 11481 (2015)
  188. M.-Z.Lu, C.-Q.Wang, T.-P.Loh. Org. Lett., 17, 6110 (2015)
  189. H.Zhou, W.Jian, B.Qian, C.Ye, D.Li, J.Zhou, H.Bao. Org. Lett., 19, 6120 (2017)
  190. Y.-A.Yuan, D.-F.Lu, Y.-R.Chen, X.Hao. Angew. Chem., Int. Ed., 55, 534 (2016)
  191. H.-T.Zhu, L.Arosio, R.Villa, M.Nebuloni, H.Xu. Org. Process Res. Dev., 21, 2068 (2017)
  192. S.-J.Shen, C.-L.Zhu, D.-F.Lu, H.Xu. ACS Catal., 8, 4473 (2018)
  193. H.Li, S.J.Shen, C.L.Zhu, H.Xu. J. Am. Chem. Soc., 140, 10619 (2018)
  194. H.Peng, Zh.Yuan, P.Chen, G.Liu. Chin. J. Chem., 35, 876 (2017)
  195. T.R.Reddy, D.S.Rao, S.Kashyap. Chem. Commun., 55, 2833 (2019)
  196. N.Fu, G.S.Sauer, A.Saha, A.Loo, S.Lin. Science, 357, 575 (2017)
  197. J.Wu, Y.Dou, R.Guillot, C.Kouklovsky, G.Vincent. J. Am. Chem. Soc., 141, 2832 (2019)
  198. N.Fu, G.S.Sauer, S.Lin. Nat. Protoc., 13, 1725 (2018)
  199. J.C.Siu, J.B.Parry, S.Lin. J. Am. Chem. Soc., 141, 2825 (2019)
  200. M.Mali, V.Jayaram, G.V.M.Sharma, S.Ghosh, F.Berree, V.Dorcet, B.Carboni. J. Org. Chem., 85, 15104 (2020)
  201. J.R.Fotsing, M.Hagedorn, K.Banert. Tetrahedron, 61, 8904 (2005)
  202. S.V.Chapyshev, A.V.Chernyak. J. Fluorine Chem., 156, 303 (2013)
  203. R.Weiss, F.G.Puhlhofer, S.M.Huber. Eur. J. Org. Chem., 5270 (2007)
  204. I.M.Takakis, P.M.Hadjimihalakis. J. Heterocycl. Chem., 28, 1373 (1991)
  205. A.Y.Tyurin, A.M.Churakov, Y.A.Strelenko, M.O.Ratnikov, V.A.Tartakovsky. Russ. Chem. Bull., Int. Ed., 55, 1648 (2006)
  206. R.Adams, W.Moje. J. Am. Chem. Soc., 74, 5560 (1952)
  207. H.Nakazumi, K.Kondo, T.Kitao. Synthesis, 878 (1982)
  208. W.L.Mosby, M.L.Silva. J. Chem. Soc., 3990 (1964)
  209. C.Erasmus, J.Aucamp, F.J.Smit, R.Seldon, A.Jordaan, D.F.Warner, D.D.N'Da. Bioorg. Chem., 114, 105118 (2021)
  210. D.S.Pearce, M.-S.Lee, H.W.Moore. J. Org. Chem., 39, 1362 (1974)
  211. D.J.Shields, S.K.Sarkar, H.D.M.Sriyarathne, J.R.Brown, C.Wentrup, M.Abe, A.D.Gudmundsdottir. Org. Lett., 21, 7194 (2019)
  212. D.Sun, W.H.Watson. J. Org. Chem., 62, 4082 (1997)
  213. Y.Hosoya, W.Nojo, I.Kii, T.Suzuki, M.Imanishi, J.Ohkanda. Chem. Comm., 56, 11203 (2020)
  214. J.A.Van Allan, W.J.Priest, A.S.Marshall, G.A.Reynolds. J. Org. Chem., 33, 1100 (1968)
  215. M.Novak, A.M.Brinster, J.N.Dickhoff, J.M.Erb, M.P.Jones, S.H.Leopold, A.T.Vollman, Y.-T.Wang, S.A.Glover. J. Org. Chem., 72, 9954 (2007)
  216. E.Winkelmann. Tetrahedron, 25, 2427 (1969)
  217. U.C.Singh, M.S.Ramachandran, N.R.Subbaratnam, V.K.Kelkar. Spectrochim. Acta, Part A, 35, 663 (1979)
  218. W.H.Gilligan, M.J.Kamlet. Tetrahedron Lett., 19, 1675 (1978)
  219. H.W.Moore, D.L.Maurer, D.S.Pearce, M.S.Lee. J. Org. Chem., 37, 1984 (1972)
  220. H.-W.Yoo, M.-E.Suh, S.W.Park. J. Med. Chem., 41, 4716 (1998)
  221. J.H.Hall, E.Patterson. J. Am. Chem. Soc., 89, 5856 (1967)
  222. J.H.Hall. J. Am. Chem. Soc., 87, 1147 (1965)
  223. W.L.Mosby, M.L.Silva. J. Chem. Soc., 1003 (1965)
  224. M.E.Peek, C.W.Rees, R.C.Storr. J. Chem. Soc., Perkin Trans. 1, 1260 (1974)
  225. S.P.Klump, H.Shechter. Tetrahedron Lett., 43, 8421 (2002)
  226. M.Horner, H.Fenner, W.Hiller, J.Beck. Z. Naturforsch., Sect. B, 43, 1174 (1988)
  227. A.Mishra, V.Tiwari. J. Org. Chem., 80, 4869 (2015)
  228. I.A.Shehata. Monatsh. Chem., 121, 1017 (1990)
  229. S.K.Kotovskaya, S.A.Romanova, V.N.Charushin, O.N.Chupakhin. Russ. J. Org. Chem., 38, 1046 (2002)
  230. S.V.Chapyshev, D.V.Korchagin, Y.V.Ganin, E.N.Ushakov. Chem. Heterocycl. Compd., 53, 786 (2017)
  231. Y.M.Mikhailov, S.V.Chapyshev, V.V.Nedel'ko. Russ. Chem. Bull., Int. Ed., 58, 2097 (2009)
  232. S.Kagabu, P.Maienfisch, A.Zhang, J.Granda-Minones, J.Haettenschwiler, H.Kayser, T.Maetzke, J.E.Casida. J. Med. Chem., 43, 5003 (2000)
  233. Y.Mao, I.Maley, W.H.Watson. J. Chem. Crystallogr., 35, 385 (2005)
  234. A.Mustafa, S.M.A.D.Zayed, S.Khattab. J. Am. Chem. Soc., 78, 145 (1956)
  235. T.Watanabe, I.Ueda, N.Hayakawa, Y.Kondo, H.Adachi, A.Iwasaki, S.Kawamata, F.Mentori, M.Ichikawa, K.Yuasa, A.Ohta, T.Kurihara, H.Miyamae. J. Heterocycl. Chem., 27, 711 (1990)
  236. N.Sato, T.Matsuura, N.Miwa. Synthesis, 931 (1994)
  237. C.D.Campbell, C.W.Rees. Chem. Commun. (London), 10, 192 (1965)
  238. A.Yabe. Bull. Chem. Soc. Jpn., 54, 1176 (1981)
  239. H.C.Van der Plas. Ring Transformation of Heterocycles. (London: Academic Press, 1973)
  240. T.Watanabe, J.Nishiyama, R.Hirate, K.Uehara, M.Inoue, K.Matsumoto, A.Ohta. J. Heterocycl. Chem., 20, 1277 (1983)
  241. S.Guillou, G.Jacob, F.Terrier, R.Goumont. Tetrahedron, 65, 8891 (2009)
  242. K.Banert, F.Kohler. Angew. Chem., Int. Ed., 40, 174 (2001)
  243. K.Banert, J.R.Fotsing, M.Hagedorn, H.P.Reisenauer, G.Maier. Tetrahedron, 64, 5645 (2008)
  244. S.G.Bodige, M.A.Mendez-Rojas, W.H.Watson. J. Chem. Crystallogr., 29, 57 (1999)
  245. P.Molina, A.Arques, M.V.Vinader. J. Org. Chem., 55, 4724 (1990)
  246. C.K.Ryu, S.Y.Oh, S.J.Choi, D.Y.Kang. Chem. Pharm. Bull., 62, 1119 (2014)
  247. C.Borriello, A.De Renzi, M.Fusto, A.Molinaro, F.Ruffo. Carbohydr. Res., 331, 209 (2001)
  248. V.Popsavin, G.Benedekovic, M.Popsavin, D.Miljkovic. Carbohydr. Res., 337, 459 (2002)
  249. V.Popsavin, G.Benedekovic, M.Popsavin, V.Divjakovic, T.Armbruster. Tetrahedron, 60, 5225 (2004)
  250. M.Saito, Y.Kayama, T.Watanabe, H.Fukushima, T.Hara, K.Koyano, Y.Sasada. J. Med. Chem., 23, 1364 (1980)
  251. M.Boge, C.Fowelin, P.Bednarski, J.Heck. Organometallics, 34, 1507 (2015)
  252. A.Trapero, A.Llebaria. ACS Med. Chem. Lett., 2, 614 (2011)
  253. R.Gust, T.Burgemeister, A.Mannschreck, H.Schoenenberger. J. Med. Chem., 33, 2535 (1990)
  254. R.Hilgraf, A.Pfaltz. Adv. Synth. Catal., 347, 61 (2005)
  255. T.C.Tompkins, P.H.Gross. J. Org. Chem., 47, 2691 (1982)
  256. P.Sivaguru, Y.Ning, X.Bi. Chem. Rev., 121, 4253 (2021)
  257. S.-G.Lee, C.Lim, C.Song, I.Kim, C.-H.Jun. Tetrahedron: Asymmetry, 8, 2927 (1997)
  258. C.Bit, A.A.Mitrochkine, G.Gil, P.Mierrot, M.Reglier. Tetrahedron: Asymmetry, 9, 3263 (1998)
  259. M.J.Palmer, J.A.Kenny, T.Walsgrove, A.M.Kawamoto, M.Wills. J. Chem. Soc., Perkin Trans. 1, 416 (2002)
  260. P.Magnus, J.Lacour. J. Am. Chem. Soc., 114, 767 (1992)
  261. A.Mochizuki, Y.Nakamoto, H.Naito, K.Uoto, T.Ohta. Bioorg. Med. Chem. Lett., 18, 782 (2008)
  262. M.Hashimoto, K.Furukawa, T.Tomohiro, Y.Hatanaka. Chem. Pharm. Bull., 58, 405 (2010)
  263. C.W.Zapf, J.D.Bloom, Z.Li, R.G.Dushin, T.Nittoli, M.Otteng, J.I.Levin. Bioorg. Med. Chem. Lett., 21, 4602 (2011)
  264. Y.Noritake, N.Umezawa, N.Kato, T.Higuchi. Inorg. Chem., 52, 3653 (2013)
  265. L.Lascialfari, G.Pescitelli, A.Brandi, M.Mannini, D.Berti, S.Cicchi. Soft Matter, 11, 8333 (2015)
  266. O.Kaya, M.E.engul, A.Menzek, E.ahin, B.Gur. Tetrahedron, 72, 2828 (2016)
  267. A.Jirkovska, G.Karabanovich, J.Kubes, V.Skalicka, I.Melnikova, J.Korabecny, T.Kucera, E.Jirkovsky, L.Novakova, H.B.Piskackova, J.Skoda, M.Sterba, C.A.Austin, T.Simunek, J.Roh. J. Med. Chem., 64, 3997 (2021)
  268. C.Camp, S.Dorbes, C.Picard, E.Benoist. Tetrahedron Lett., 49, 1979 (2008)
  269. V.O.Rodionov, V.V.Fokin, M.G.Finn. Angew. Chem., Int. Ed., 44, 2210 (2005)
  270. F.Yu, Y.Peng, Q.Wang, Y.Shi, L.Si, H.Wang, D.Zhou. Eur. J. Med. Chem., 77, 258 (2014)
  271. M.Oba, N.Kawabe, H.Takazaki, Y.Demizu, M.Doi, M.Kurihara, M.Tanaka. Tetrahedron, 70, 8900 (2014)
  272. V.B.Sokolov, A.Y.Aksinenko, T.A.Epishina. Russ. Chem. Bull., Int. Ed., 67, 1401 (2018)
  273. K.Kiran, M.Sarasija, B.A.Rao, A.Jeyanthi, A.S.Rao, D.Ashok. Russ. J. Gen. Chem., 88, 2410 (2018)
  274. S.Tejera, G.Caniglia, R.L.Dorta, A.Favero, J.Gonzalez- Platas, J.T.Vazquez. Beilstein J. Org. Chem., 15, 2881 (2019)
  275. C.Wang, D.Wang, S.Yu, T.Cornilleau, J.Ruiz, L.Salmon, D.Astruc. ACS Catal., 6, 5424 (2016)
  276. H.Priebe. Angew. Chem., Int. Ed. Engl., 23, 736 (1984)
  277. K.Banert, M.Hagedorn. Angew. Chem., Int. Ed. Engl., 28, 1675 (1989)
  278. P.Klaeboe, C.J.Nielson, H.Priebe, S.H.Schei, C.E.Sjcrgen. J. Mol. Struct., 141, 161 (1986)
  279. C.J.Nielson, P.Klaeboe, H.Priebe. J. Mol. Struct., 147, 217 (1986)
  280. K.Banert. Angew. Chem., Int. Ed. Engl., 26, 879 (1987)
  281. K.Banert. Chem. Ber., 122, 123 (1989)
  282. K.Banert. Tetrahedron Lett., 26 (43), 5261 (1985)
  283. K.Banert. Chem. Ber., 120, 1891 (1987)
  284. H.Roesky, O.Glemser. Chem. Ber., 97, 1710 (1964)
  285. F.Liu, X.Zeng, Q.Sun, L.Meng, S.Zheng, X.Ai, J.Zhang, M.Ge, D.Wang. Bull. Chem. Soc. Jpn., 78, 1246 (2005)
  286. A.G.Harter, T.M.Klapotke, J.Stierstorfer, M.Voggenreiter, X.Zeng. ChemPlusChem, 86, 870 (2021)
  287. I.Tselinskii, S.Mel'nikova, T.Romanova. Russ. J. Org. Chem., 37, 430 (2001)
  288. X.J.Wang, Q.Su, L.J.Li, S.H.Jin, H.Niu, S.S.Chen, Q.H.Shu. J. Heterocycl. Chem., 54, 2228 (2017)
  289. X.Wang, S.Jin, C.Zhang, L.Li, S.Chen, Q.Shu. Chin. J. Chem., 33, 1229 (2015)
  290. W.H.Lee, K.Kwon. Propellants Explos. Pyrotech., 44, 1478 (2019)
  291. Patent KR 101964988B1 (2019)
  292. Patent CN 104151195A (2014)
  293. Appl. US 2020/0039895A1 (2020)
  294. M.B.Talawar, S.Nandagopal, S.Singh, A.P.Mahajan, D.M.Badgujar, M.Gupta, Md.A.S.Khan. ChemistrySelect, 3, 12175 (2018)
  295. Appl. US 2021/0163428A1 (2021)
  296. Patent KR 102331641B1 (2021)
  297. Patent KR 102331642B1 (2021)
  298. Patent US 2021403441A1 (2021)
  299. H.-J.Ha, B.Kim, K.Kwon, S.H.Kim, C.-W.Cho. Propellants Explos. Pyrotech., 46, 732 (2021)
  300. P.He, J.Liu, J.Wu, H.Mei, J.Zhang. Chem.-Asian J., 14, 3845 (2019)
  301. N.Szimhardt, M.F.Bolter, M.Born, T.M.Klapotke, J.Stierstorfer. Dalton Trans., 46, 5033 (2017)
  302. P.He, L.Wu, J.Wu, Q.Wang, Z.Li, M.Gozin, J.Zhang. Chem.-Eur. J., 23, 11159 (2017)
  303. D.Fischer, T.M.Klapotke, J.Stierstorfer. Angew. Chem., Int. Ed., 53, 8172 (2014)
  304. U.Muller, K.Dehnicke. Angew. Chem., Int. Ed. Engl., 5, 841 (1966)
  305. M.A.Petrie, J.A.Sheehy, J.A.Boatz, G.Rasul, G.K.S.Prakash, G.A.Olah, K.O.Christe. J. Am. Chem. Soc., 119, 8802 (1997)
  306. A.Hassner, M.Stern, H.E.Gottlieb, F.Frolow. J. Org. Chem., 55, 2304 (1990)
  307. K.A.Lyssenko, Y.V.Nelubina, D.V.Safronov, O.I.Haustova, R.G.Kostyanovsky, D.A.Lenev, M.Y.Antipin. Mendeleev Commum., 15, 232 (2005)
  308. Patent US 4683086A (1987)
  309. Y.-H.Joo, J.M. Shreeve. Chem. Commun., 46, 142 (2010)
  310. T.Lenz, T.M.Klapotke, M.Muhlemann, J.Stierstorfer. Propellants Explos. Pyrotech., 46, 723 (2021)
  311. N.Lease, L.M.Kay, G.W.Brown, D.E.Chavez, D.Robbins, E.F.C.Byrd, G.H.Imler, D.A.Parrish, V.W.Manner. J. Org. Chem., 85, 4619 (2020)
  312. Y.Tang, J.M.Shreeve. Chem.-Eur. J., 21, 7285 (2015)
  313. L.Bauer, M.Benz, T.M.Klapotke, T.Lenz, J.Stierstorfer. J. Org. Chem., 86, 6371 (2021)
  314. M.Wieland, K.-J.Su, G.Wagner, U.H.Brinker, V.B.Arion. Acta Crystallogr., Sect. C, 65, o240 (2009)
  315. W.R.Martin, D.W.Ball. ChemistrySelect, 3, 7222 (2018)
  316. T.M.Klapotke, F.A.Martin, J.Stierstorfer. Angew. Chem., Int. Ed., 50, 4227 (2011)
  317. T.M.Klapotke, B.Krumm, F.A.Martin, J.Stierstorfer. Chem.-Asian J., 7, 214 (2012)
  318. K.Banert, S.Richter, D.Schaarschmidt, H.Lang. Angew. Chem., Int. Ed., 52, 3499 (2013)
  319. C.Grundmann. In Houben-Weyl, Methoden der Organischen Chemie. (4th Edn.), Vol. 10/3. (Stuttgart: Thieme, 1965). P. 777
  320. P.Klahn, H.Erhardt, A.Kotthaus, S.F.Kirsch. Angew. Chem., Int. Ed., 53, 7913 (2014)
  321. S.V.Chapyshev. Molecules, 20, 19142 (2015)
  322. S.V.Chapyshev. Russ. Chem. Bull., Int. Ed., 60, 1274 (2011)
  323. Patent DE 498050 (1927)
  324. F.P.Bowden, H.T.Williams. Proc. R. Soc. A, 208, 176 (1951)
  325. A.S.Bailey, J.R.Case. Tetrahedron, 3, 113 (1958)
  326. O. Turek. Chim. Ind., 26, 785 (1931)
  327. S.V.Chapyshev, A.V.Chernyak. J. Fluorine Chem., 156, 303 (2013)
  328. J.G.Morse, L.P.Kuhn. US Clearinghouse Fed. Sci. Tech. Inform., IDNo. 713665(1970); Chem. Abstr., 75, 19826 (1971)
  329. S.V.Chapyshev, R.Walton, J.A.Sanborn, P.M.Lahti. J. Am. Chem. Soc., 122, 1580 (2000)
  330. K.Wallenfels, F.Wittzler, K.Friedrich. Tetrahedron, 23, 1845 (1967)
  331. M.Becker, K.Voss, A.Villinger, A.Schulz. Z. Naturforsch., Sect. B, 67, 643 (2012)
  332. R.Ranjbar-Karimi, T.Davoodian, H.Mehrabi. J. Iran. Chem. Soc., 17, 2145 (2020)
  333. M.-H.V.Huynh, M.A.Hiskey, E.L.Hartline, D.P.Montoya, R.Gilardi. Angew. Chem., 116, 5032 (2004)
  334. M.-H.V.Huynh, M.A.Hiskey, E.L.Hartline, D.P.Montoya, R.Gilardi. Angew. Chem., Int. Ed., 43, 4924 (2004)
  335. W.Zheng, N.-B.Wong, X.Liang, X.Long, A.Tian. J. Phys. Chem. A, 108, 840 (2004)
  336. L.M.Foroughi, R.A.Wiscons, D.R.Du Bois, A.J.Matzger. Chem. Commun., 56, 2111 (2020)
  337. A.Hammerl, T.M.Klapotke, R.Rocha. Eur. J. Inorg. Chem., 2210 (2006)
  338. F.Wang, H.-C.Du, H.Liu, X.-D.Gong. J. Comput. Chem., 33, 1820 (2012)
  339. S.V.Chapyshev, E.N.Ushakov, A.V.Chernyak. Magn. Reson. Chem., 51, 562 (2013)
  340. E.G.Gillan. Chem. Mater., 12, 3906 (2000)
  341. J.Wang, E.G.Gillan. Thin Solid Films, 422, 62 (2002)
  342. S.Kumar, V.R.Battula, K.Kailasam. Carbon, 183, 332 (2021)
  343. M.Lammens, F.Du Prez. Complex Macromolecular Architectures: Synthesis, Characterization, and Self-Assembly. (1st Edn.) (Wiley, 2011)
  344. J.Mandal, S.Ramakrishnan. In Click Reactions in Organic Synthesis. (1st Edn.) (Ed. S.Chandrasekaran). (Wiley-VCH, 2016). P. 203
  345. J.A.Johnson, M.G.Finn, J.T.Koberstein, N.J.Turro. Macromol. Rapid Commun., 29, 1052 (2008)
  346. K.Brunner, J.Harder, T.Halbach, J.Willibald, F.Spada, F.Gnerlich, K.Sparrer, A.Beil, L.Mockl, C.Brauchle, K.-K.Conzelmann, T.Carell. Angew. Chem., Int. Ed., 54, 1946 (2015)
  347. D.-H.Lee, K.T.Kim, Y.Jang, S.Lee, H.B.Jeon, H.Paik, B.S.Min, W.Kim. J. Appl. Polym. Sci., 131, 40594 (2014)
  348. J.Morales-Sanfrutos, M.Ortega-Munoz, J.Lopez-Jaramillo, F.Hernandez-Mateo, F.Santoyo-Gonzalez. J. Org. Chem., 73, 7772 (2008)
  349. A.R.Katritzky, N.K.Meher, S.Hanci, R.Gyanda, S.R.Tala, S.Mathai, R.S.Duran, S.Bernard, F.Sabri, S.K.Singh, J.Doskocz, D.A.Ciaramitaro. J. Polym. Sci., Part A: Polym. Chem., 46, 238 (2008)
  350. I.Nierengarten, J.-F.Nierengarten. Chem. Rec., 15, 31 (2015)
  351. K.Hiba, K.Sreekumar. React. Funct. Polym., 160, 104827 (2021)
  352. J.Wu, R.Hunter Cooke III, H.A.Livingston, G.L.Parker, B.C.Peoples, A.Ekin, R.F.Storey. Prog. Org. Coat., 151, 106079 (2021)
  353. R.Hunter Cooke III, J.Wu, H.A.Livingston, G.L.Parker, B.C.Peoples, A.Ekin, A.Bushmir, R.F.Storey. Prog. Org. Coat., 151, 106047 (2021)
  354. T.Trinh, D.Saliba, C.Liao, D.Rochambeau, A.L.Prinzen, J.Li, H.F.Sleiman. Angew. Chem., Int. Ed., 58, 3042 (2019)
  355. R.Scanga, L.Chrastecka, R.Mohammad, A.Meadows, P.-L.Quan, E.Brouzes. RSC Adv., 8, 12960 (2018)

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