Email this article 
Mass-spectrometric study of substituted (β-hydroxy-, β-acetoxy)sulfides and -sulfones of 1,3-dioxepane series using electron ionization
- Authors: Shamsutdinova L.R1, Musin R.Z1, Paveliev R.S2, Rizvanov I.K.1, Dimukhametov M.N1
-
Affiliations:
- A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
- Kazan (Volga Region) Federal University
- Issue: Vol 93, No 4 (2023)
- Pages: 539-547
- Section: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145017
- DOI: https://doi.org/10.31857/S0044460X23040066
- EDN: https://elibrary.ru/ATTCCX
- ID: 145017
Cite item
Open Access
Access granted
Subscription Access
Abstract
The electron ionization mass spectra of substituted (β-hydroxy)sulfides, -sulfones, and their corresponding acetates of the 1,3-dioxepane series were studied. The main regularities in the pathways of fragmentation of their molecular ions were revealed. It was shown that during electron ionization, the main directions of decomposition of the studied compounds are due to the elimination of substituents in the 1,3-dioxepane ring. For 6-phenylthio-1,3-dioxepanes and 6-phenylsulfonyl-1,3-dioxepanes, the formation of ions associated with the breaking of C-S bonds with charge localization on the sulfur-containing fragment is observed.
About the authors
L. R Shamsutdinova
A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
Email: leisan.shamsutdinova@iopc.ru
R. Z Musin
A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
R. S Paveliev
Kazan (Volga Region) Federal University
I. Kh. Rizvanov
A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
M. N Dimukhametov
A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
References
- Kesavan V., Bonnet-Delpon D., Begue J.-P. // Tetrahedron Lett. 2000. Vol. 41. N 16. P. 2895. doi: 10.1016/S0040-4039(00)00305-1
- Ozaki S., Matsui E., Yoshinaga H., Kitagawa S. // Tetrahedron Lett. 2000. Vol. 41. N 15. P. 2621. doi: 10.1016/S0040-4039(00)00231-8
- Begue J.-P., Bonnet-Delpon D., Kornilov A. // Synthesis. 1996. N 4. P. 529. doi: 10.1055/s-1996-4235
- Tanikaga R., Hosoya K., Kaji A. // J. Chem. Soc. Perkin Trans. 1. 1987. Vol. 1. P. 1799. doi: 10.1039/p19870001799
- Otera J., Misawa H., Sugimoto K. // J. Org. Chem. 1986. Vol. 51. N 20. P. 3830. doi: 10.1021/jo00370a016
- Achmatowicz B., Baranowska E., Daniewski A.R., Pankowski J., Wicha J. // Tetrahedron. 1988. Vol. 44. N 15. P. 4989. doi: 10.1016/s0040-4020(01)86203-7
- Furutani T., Imashiro R., Hatsuda M., Seki M. // J. Org. Chem. 2002. Vol. 67. N 13. P. 4599. doi: 10.1021/jo025647b
- Sato T., Okumura Y., Itai J., Fujisawa T. // Chem. Lett. 1988. Vol. 17. N 9. P. 1537. doi: 10.1246/cl.1988.1537
- Пат. RU 2122745 (2015).
- Pavelyev R.S., Gnevashev S.G., Vafina R.M., Gnezdilov O.I., Dobrynin A.B., Lisovskaya S.A., Nikitina L.E., Klimovitskii E.N. // Mendeleev Commun. 2012. Vol. 22. P. 127. doi: 10.1016/J.MENCOM.2012.05.003
- Pavelyev R.S., Vafina R.M., Balakin K.V., Gnezdilov O.I., Dobrynin A.B., Lodochnikova O.A., Musin R.Z., Chmutova G.A., Lisovskaya S.A., Nikitina L.E. // J. Chem. 2018. Vol. 2018. Article ID 3589342. doi: 10.1155/2018/3589342
- Павельев Р.С., Климовицкий Е.Н., Никитина Л.Е. // Химия в интересах устойчивого развития. 2010. Т. 18. Вып. 6. С. 6.
- Павельев Р.С., Гневашев С.Г., Вафина Р.М., Гнездилов О.И., Мусин Р.З., Никитина Л.Е. // Ученые записки Казанского университета. Серия Естественные науки. 2011. Т. 153. Кн. 3. С. 9.
- Мусин Р.З., Мусин Р.P., Бабаев В.М., Павельев Р.С., Климовицкий Е.Н. // Тезисы докл. 4 Всерос. конф. с междунар. участием "Масс-спектрометрия и ее прикладные проблемы". Москва, 2011. С. 39.
- Джонстон Р. Руководство по масс-спектрометрии для химиков-органиков. М.: Мир, 1975. 236 с.
- Краснокутская Е.А., Филимонов В.Д. Спектральные методы исследования в органической химии. Томск: ТПУ, 2013. Ч. 2. 88 с.
- Лебедев А.Т. Масс-спектрометрия в органической химии. М.: БИНОМ. Лаборатория знаний, 2003. 493 с.
Supplementary files
