Abstract
The free-radical rearrangement of pinocarveyl hydroperoxide (1) or myrtenyl hydroperoxide (2) in hexane produces an equilibrium mixture of both hydroperoxides. The absence of carbon skeletal rearrangement suggests that the intermediate radical involved in hydroperoxide isomerization has its unpaired electron localized elsewhere than the α-carbon atom. The failure of oxygen to react with pino-carveyl, myrtenyl, and acyclic hydroperoxides (8) and (9) during the allylic rearrangement supports this suggestion. The kinetics of the rearrangements of 1-isopropyl-2-methylallyl hydroperoxide (8) is compatible with a mechanism in which the intermediate is a common allylperoxyl radical produced directly from either allylic isomer.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
