Effect of chalcogenyl substituent on the course of allyl rearrangement at chalcogenation of 1,3-dichloropropene
- Authors: Levanova E.P.1, Nikonova V.S.1, Grabel’nykh V.A.1, Russavskaya N.V.1, Albanov A.I.1, Rozentsveig I.B.1, Korchevin N.A.1
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Affiliations:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 52, No 5 (2016)
- Pages: 615-623
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/214261
- DOI: https://doi.org/10.1134/S1070428016050018
- ID: 214261
Cite item
Abstract
Formation of 1,3-dichalcogenylpropene at the treatment of 1,3-dichloropropene with organic dichalcogenides in a redox system hydrazine hydrate–KOH is governed by the possibility of an allyl rearrangement. In the presence of bases this rearrangement proceeds via carbanion partially stabilized by the chalcogenyl substituent. The effectivity of the stabilization and consequently the probability of the rearrangement varies in the series of substituents PhS > BnS > PhSe. In the stage of the direct nucleophilic substitution of chlorine the anion PhSe‒ possesses the highest activity.
About the authors
E. P. Levanova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
V. S. Nikonova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
V. A. Grabel’nykh
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Author for correspondence.
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. V. Russavskaya
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. I. Albanov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
I. B. Rozentsveig
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. A. Korchevin
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: venk@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
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