Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

I. A. Novakov; B. S. Orlinson; E. N. Savel’ev; E. A. Potaenkova; O. V. Vostrikova; D. P. Tarakanov; M. A. Nakhod

doi:10.1134/S1070363217120027

Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

Authors: Novakov I.A.¹, Orlinson B.S.¹, Savel’ev E.N.¹, Potaenkova E.A.¹, Vostrikova O.V.¹, Tarakanov D.P.¹, Nakhod M.A.¹
Affiliations:
1. Volgograd State Technical University
Issue: Vol 87, No 12 (2017)
Pages: 2762-2765
Section: Article
URL: https://journals.rcsi.science/1070-3632/article/view/221673
DOI: https://doi.org/10.1134/S1070363217120027
ID: 221673

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Abstract

The Willgerodt–Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography–mass spectrometry. The reaction time was found to be 3–4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.