Organic letters

1, 6-Methano [10] annulene-stabilized radicals

X Creary, KM Miller

Index: Creary, Xavier; Miller, Kevin M. Organic Letters, 2002 , vol. 4, # 20 p. 3493 - 3496

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Citation Number: 6

Abstract

The rate of the methylenecyclopropane rearrangement is remarkably enhanced by the 1, 6- methano [10] annulene group, which greatly stabilizes the biradical intermediate. The diastereomeric products argue against a concerted rearrangement mechanism and support a stabilized biradical intermediate that lives long enough to undergo rotation before ring closure.