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 journalArticle

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.

LanguageEnglish
Pages1371-1372
Number of pages2
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
DOIs
Publication statusPublished - 1 Dec 1993
Externally publishedYes

Fingerprint

Lewis Acids
Nucleophiles
Sulfides
Nitrogen
Ions
Isomerization

Cite this

@article{a497c65deb0f461ab834e671a9d39c8d,
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",
month = "12",
day = "1",
doi = "10.1039/P19930001371",
language = "English",
pages = "1371--1372",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "0300-922X",
publisher = "Chemical Society",
number = "13",

}

TY - JOUR

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

T2 - Journal of the Chemical Society, Perkin Transactions 2

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 - http://www.scopus.com/inward/record.url?scp=37049067185&partnerID=8YFLogxK

U2 - 10.1039/P19930001371

DO - 10.1039/P19930001371

M3 - Article

SP - 1371

EP - 1372

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 0300-922X

IS - 13

ER -