Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones


Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A green approach was proposed for the synthesis of 2-chloroprop-2-en-1-yl sulfones in 47–94% yield. The molecular and crystal structures of 2-chloroprop-2-en-1-yl phenyl sulfone and 2-chloroprop-2-en-1-yl methyl sulfone were determined by X-ray analysis. π-Stacking interaction between the benzene ring and double bond was revealed in the crystal structure of 2-chloroprop-2-en-1-yl phenyl sulfone. Chloropropenyl sulfones were found to readily undergo dehydrochlorination to give stable allenyl sulfones and alkaline hydrolysis to produce the corresponding acetonyl sulfones. The latter can be converted to oximes by treatment with hydroxylamine hydrochloride.

About the authors

V. S. Nikonova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Author for correspondence.
Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

A. R. Kaliev

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

T. N. Borodina

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

V. I. Smirnov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

I. B. Rozentsveig

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

N. A. Korchevin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: vachrina@irioch.irk.ru
Russian Federation, Irkutsk, 664033

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2019 Pleiades Publishing, Ltd.