Australian journal of chemistry

Orbital interactions. XII. Product studies and competition kinetic measurements of the Birch reduction of a series of hexahydrodimethanonaphthalenes and their …

DD Chau, MN Paddon-Row, HK Patney

Index: Chau, Diem Dieu; Paddon-Row, Michael N.; Patney, Harish K. Australian Journal of Chemistry, 1983 , vol. 36, # 12 p. 2423 - 2446

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Citation Number: 5

Abstract

Abstract Relative rate constants for the Birch reduction (Li/liq. NH 3/Bu t OH) of the three isomeric hexahydrodimethanonaphthalenes (3)-(5) and the octahydro analogues (10)-(13) were obtained and compared with those obtained for the reduction of norbornadiene and norbornene from an earlier study. Diene (5) was reduced almost 2000 times more rapidly than norbornene and 20000 times more rapidly than the monoene (13). Rate- ...