The effect of strain on the rearrangement of allylic hydroperoxides: A research account

Aryeh A. Frimer

doi:10.1016/0047-2670(84)87025-2

The effect of strain on the rearrangement of allylic hydroperoxides: A research account

Aryeh A. Frimer

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

While strain seems to play a minor role at most in directing singlet oxygen (¹O₂) reactions, it does have a profound effect on the secondary rearrangements of allylic hydroperoxides formed in the photosensitized oxidation of small ring systems. The abundance of products formed in the photo-oxidation of alkylidenecyclopropanes and cyclopropenes can be rationalized for the most part on the basis of various "Hock cleavage" processes in which strain is the dominant consideration determining the ordering of migratory aptitudes and product distribution.

Original language	English
Pages (from-to)	211-226
Number of pages	16
Journal	Journal of Photochemistry
Volume	25
Issue number	2-4
DOIs	https://doi.org/10.1016/0047-2670(84)87025-2
State	Published - Jun 1984

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AB - While strain seems to play a minor role at most in directing singlet oxygen (1O2) reactions, it does have a profound effect on the secondary rearrangements of allylic hydroperoxides formed in the photosensitized oxidation of small ring systems. The abundance of products formed in the photo-oxidation of alkylidenecyclopropanes and cyclopropenes can be rationalized for the most part on the basis of various "Hock cleavage" processes in which strain is the dominant consideration determining the ordering of migratory aptitudes and product distribution.

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The effect of strain on the rearrangement of allylic hydroperoxides: A research account

Abstract

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