A Cyclopropyl??Homoallyl Rearrangement Accompanying the Borane??Mediated Reduction of Tosylhydrazones

…, J Muharemspahić, K Mlinarić??Majerski

文献索引：Kragol, Goran; Benko, Iva; Muharemspahic, Jasmina; Mlinaric-Majerski, Kata European Journal of Organic Chemistry, 2003 , # 14 p. 2622 - 2625

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被引用次数: 4

摘要

Abstract The Wolff− Kishner reduction of strained cyclopropyl ketones 9-oxo-2, 8- didehydronoradamantane (1) and 5-oxo-2, 4-didehydrobrendane (5) proceeds without rearrangement, while the borane-mediated reduction of the corresponding tosylhydrazones 1a and 5a affords the rearranged products tricyclo [4.2. 1.0 3, 8] non-4-ene (3) and 4- brendene (7), respectively. Rearrangement also occurs during the reduction of the less- ...