Regioselectivity in the reductive cleavage of syn-and anti-2-methylspiro [cyclopropane-1, 1'-indene]. Elucidation of the role of steric effects

SW Staley, MA Fox, TK Hirzel

文献索引：Staley,S.W. et al. Journal of the American Chemical Society, 1976 , vol. 98, # 13 p. 3910 - 3916

全文：HTML全文

被引用次数: 5

摘要

Abstract: The title compounds (11 and 12, respectively) have been shown to suffer reductive cleavage at essentially the same rate on treatment with lithium or sodium in liquid ammonia at ca.-33 OC. Six cyclopropyl ring-opened products have been identified as products of this reaction. The regioselectivity [opening of bond a relative to bond b (ka/kb)] is 4 for 11 and 0.6 for 12 (in lithium-liquid ammonia). These opposite regioselectivites are explained in part ...