Tetrahedron

β'β Anionic elimination of carboxylic esters

C Aubert, JP Bégué, JF Biellmann

Index: Aubert, Corinne; Begue, Jean-Pierre; Biellmann, Jean-Francois Tetrahedron, 1986 , vol. 42, # 20 p. 5581 - 5590

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Citation Number: 3

Abstract

The elimination of lithium, magnesium and aluminium enolatea of isobutyrates of medium ring cyclanols occurs in a syn fashion. A set of experimental procedures is presented. This elimination seems to be restricted to strained systems. The stereo-chemistry has been determined on stereospecifically deuterated cyclooctanol isobutyrates. The primary isotope effect kH/k2 was 3.0±0.1 and the secondary 1.1. The name β'β elimination is proposed for ...

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