Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles

Duncan M. Gill; Neil A. Pegg; Christopher M. Rayner

doi:10.1039/P19930001371

Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles

Duncan M. Gill, Neil A. Pegg, Christopher M. Rayner

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.

Original language	English
Pages (from-to)	1371-1372
Number of pages	2
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	13
DOIs	https://doi.org/10.1039/P19930001371
Publication status	Published - 1 Dec 1993
Externally published	Yes

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title = "Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles",

abstract = "The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.",

author = "Gill, \{Duncan M.\} and Pegg, \{Neil A.\} and Rayner, \{Christopher M.\}",

year = "1993",

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Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles. / Gill, Duncan M.; Pegg, Neil A.; Rayner, Christopher M.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 13, 01.12.1993, p. 1371-1372.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Lewis acid-induced rearrangement of 2,3-epoxy sulfides

T2 - Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles

AU - Gill, Duncan M.

AU - Pegg, Neil A.

AU - Rayner, Christopher M.

PY - 1993/12/1

Y1 - 1993/12/1

N2 - The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.

AB - The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.

UR - https://www.scopus.com/pages/publications/37049067185

U2 - 10.1039/P19930001371

DO - 10.1039/P19930001371

M3 - Article

AN - SCOPUS:37049067185

SN - 1472-7781

SP - 1371

EP - 1372

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 13

ER -

Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles

Abstract

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