Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones
- Authors: Nikonova V.S.1, Kaliev A.R.1, Borodina T.N.1, Smirnov V.I.1, Rozentsveig I.B.1, Korchevin N.A.1
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Affiliations:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 55, No 12 (2019)
- Pages: 1912-1917
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/221483
- DOI: https://doi.org/10.1134/S1070428019120170
- ID: 221483
Cite item
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
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