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

P Müller, JC Rossier

Index: Mueller, Paul; Rossier, Jean-Claude Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 11 p. 2232 - 2237

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Citation Number: 8

Abstract

The solvolysis of (R)-3-chloro-3, 7-dimethyloctane (2), of the corresponding hydrogen phthalate (S)-4g, and of the p-nitrobenzoate (S [hair space])-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.