Synlett

Designed Rearrangement of a Spirodiepoxide

Z Wang, N Shangguan, JR Cusick, LJ Williams

Index: Wang, Zhenghua; Shangguan, Ning; Cusick, Joseph R.; Williams, Lawrence J. Synlett, 2008 , # 2 p. 213 - 216

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Citation Number: 14

Abstract

Key elements of the experimental design are depicted in Scheme [3] . Where relevant, a spirodiepoxide (II) should be polarizable at the more substituted terminus under the action of a Brønsted or Lewis acid, and the corresponding carbocation should form upon full ionization (not shown). Substrates with a suitably disposable group (X) adjacent to this site would spontaneously jettison the group and thus form a double bond (III). This process could be stepwise or concerted. Aryl- ...