Stereochemistry and mechanism of pinacol-type rearrangements in the 1-phenyl-4-t-butylcyclohexane series
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 9,p. 1168-1172
- https://doi.org/10.1039/j39700001168
Abstract
The two diastereoisomeric 1,2-epoxy-1-phenyl-4-t-butylcyclohexanes and the corresponding four diols are converted into mixtures of 2-phenyl-5-t-butylcyclohexanones and 1-phenyl-3-t-butylcyclopentanecarbaldehydes by boron trifluoride–ether complex. The steric course of these reactions is interpreted in terms of a mechanism involving open carbonium ion intermediates for the diols, whereas the rearrangement of the epoxides appears to be more concerted. The silver oxide-promoted rearrangements of the cis-chlorohydrins of the same series seem to be entirely concerted.Keywords
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