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Stereochemistry and mechanism of pinacol-type rearrangements in the 1-phenyl-4-t-butylcyclohexane series
- Source :
- Journal of the Chemical Society C: Organic. :1168
- Publication Year :
- 1970
- Publisher :
- Royal Society of Chemistry (RSC), 1970.
-
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.
Details
- ISSN :
- 00224952
- Database :
- OpenAIRE
- Journal :
- Journal of the Chemical Society C: Organic
- Accession number :
- edsair.doi...........84bcd930af49059dd32e56fa94e8693c