The Journal of Organic Chemistry

Solvolytic hydroperoxide rearrangements. 2. Oxa bicyclic hemiketal peroxides from homoallylic and cyclopropylcarbinyl precursors

TS Lillie, RC Ronald

Index: Lillie, Thomas S.; Ronald, Robert C. Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5084 - 5088

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Citation Number: 13

Abstract

Studies in this laboratory have resulted in the discovery of a novel hydrogen peroxide mediated ring expansion that is suitable for the synthesis of medium to large ring oxa bicyclic compounds. This rearrangement involves the solvolysis of homoallylic brosylates or spiro cyclopropyl carbinols in THF-H2O2 and results in a two-carbon ring expansion producing hydroxy ketone derivatives in excellent yields. The reaction involves initial ...

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