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Epoxidation by dimethyldioxirane. Electronic and steric effects

✍ Scribed by Baumstark, A. L.; Vasquez, P. C.

Book ID
121288809
Publisher
American Chemical Society
Year
1988
Tongue
English
Weight
432 KB
Volume
53
Category
Article
ISSN
0022-3263

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πŸ“œ SIMILAR VOLUMES

Epoxidation of allylic hydroperoxides by
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## Abstract The epoxidation of allylic hydroperoxides 2a–h by dimethyldioxirane afforded the epoxy hydroperoxides 3a–h in very good yields. On the other hand, only the substrates 2a, b and 2d–f can be converted into the corresponding epoxy hydroperoxides by peroxy acids in reasonable to good yields

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The steric effects of allylic substituents in the epoxidations bonding is ineffective and steric interactions cause a higher trans selectivity. The conformationally fixed cis-and trans-with methyltrioxorhenium/urea/hydrogen peroxide adduct (MTO/UHP) have been assessed for a series of 3-alkyl-5-tert-