Mechanism of the triphenylphosphine-tetrachloromethane-alcohol reaction: pericyclic or clustered ion pairs?

JD Slagle, TTS Huang, B Franzus

Index: Slagle, J. D.; Huang, T. T.-S.; Franzus, B. Journal of Organic Chemistry, 1981 , vol. 46, # 17 p. 3526 - 3530

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Citation Number: 69

Abstract

The intermediate formed from tetrachloromethane-triphenylphosphine and neopentyl alcohol decomposes bimolecularly in acetonitrile and not unimolecularly as in CDC13. This kinetic order is not consistent with a pericyclic pathway but is consistent with an ion-pair mechanism. Consistent with the ion-pair mechanism in acetonitrile is the incorporation of external nucleophiles in the neopentyl skeleton by addition of added nucleophiles to the ...