Issue 3, 1987

Evidence for syn stereochemistry in intramolecular SN′ reaction of allylic acetates

Abstract

Reaction of the anion of the (R*,S*) and (R*,S*) isomers of dimethyl (E-5-acetoxyhex-3-en-2-yl)malonate [(R*,R*)-(1) and (R*,S*)-(1)] in refluxing dimethoxyethane results in an intramolecular SN′ reaction, where the displacement of the acetate by the carbanion proceeds with syn stereochemistry (94–96%syn).

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1987, 159-160

Evidence for syn stereochemistry in intramolecular SN′ reaction of allylic acetates

J. E. Bäckvall, J. O. Vågberg and J. P. Genêt, J. Chem. Soc., Chem. Commun., 1987, 159 DOI: 10.1039/C39870000159

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