The Mechanism of the Mitsunobu Reaction. III. The Use of Tributylphosphine
- 1 January 1992
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 45 (1) , 47-55
- https://doi.org/10.1071/ch9920047
Abstract
31P n.m.r . studies indicate that, when tributylphosphine is used in the Mitsunobu esterification reaction, clean formation of a single intermediate, an alkoxyphosphonium carboxylate, is apparent. In the absence of acid, at least two species are observed, a dialkoxytributylphoshorane and the corresponding alkoxyphosphonium salt. The order of mixing of the reagents can dramatically change the mechanism and stereochemistry of esterification reactions.Keywords
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