NEW SYNTHETIC REACTIONS BASED ON 1-METHYL-2-FLUOROPYRIDINIUM SALTS. FACILE CONVERSION OF ALCOHOLS TO THIOALCOHOLS

5 February 1977

journal article
research article
Published by Oxford University Press (OUP) in Chemistry Letters

Vol. 6 (2) , 133-136
https://doi.org/10.1246/cl.1977.133

Abstract

Facile conversion of alcohols to thioalcohols via thiolesters is described. The synthetic scheme involves (i) preparation of thiolesters (5) by the reaction of ethanethioate anion with 2-alkyloxypyridinium salts (3), formed from 1-methyl-2-fluoropyridinium salt (1) and alcohols, and (ii) subsequent reduction of 5 to thioalcohols. A clean inversion of configuration is noted.

Keywords

SALT
THIOALCOHOLS
FLUOROPYRIDINIUM
METHYL
ETHANETHIOATE
ANION
CONFIGURATION
NOTED
SCHEME
ALKYLOXYPYRIDINIUM

This publication has 2 references indexed in Scilit:

OPTICAL INTERCONVERSION OF ENANTIOMERIC SECONDARY ALCOHOLS USING 2-FLUOROBENZOTHIAZOLIUM SALT
Chemistry Letters, 1976
Axial and equatorial thiols
Tetrahedron, 1964