Issue 11, 2000

Solvent effects on the steric course of the solvolysis of tertiary acyclic derivatives

Abstract

The solvolysis of (R)-3-chloro-3,7-dimethyloctane (2), of the corresponding hydrogen phthalate (S)-4g, and of the p-nitrobenzoate (S )-4h proceeds with up to 87% inversion of configuration in solvents such as methanol or ethanol. The degree of inversion decreases in more dissociating solvents. In 2,2,2-trifluoroethanol (TFE), up to 40% retention of configuration occurs.

Article information

Article type
Paper
Submitted
19 Jun 2000
Accepted
30 Aug 2000
First published
18 Oct 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 2232-2237

Solvent effects on the steric course of the solvolysis of tertiary acyclic derivatives

P. Müller and J. Rossier, J. Chem. Soc., Perkin Trans. 2, 2000, 2232 DOI: 10.1039/B004884O

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