Stereochemistry of α-halogeno-sulphoxides. Part 5. Absolute stereochemistry of α-chlorination of benzyl t-butyl sulphoxide
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 1052-1056
- https://doi.org/10.1039/p19770001052
Abstract
α-Halogenation of benzyl t-butyl sulphoxide (2) by electrophilic halogenating agents in pyridine affords a mixture of the diasteroisomeric α-halogenobenzyl t-butyl sulphoxides in the ratio 5:1. In the case of the (R)-sulphoxide (2), chlorination involves selective replacement of the pro-R-hydrogen atom and occurs both with inversion at sulphur and retention at carbon (major path) and with retention at both sulphur and carbon (minor path).Keywords
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