Reaction of 3,5-Dehydronoriceane with Tetracarbonylbis(μ-chloro)dirhodium : Evidence for the Oxidative Addition of Rh(I) Complex to a Bicyclopentane System

Article abstract of DOI:10.1021/jo00197a025

A stoichiometric reaction of the title compound (1) with Rh2(CO)4Cl2 gives a stable acylrhodium complex (3).This is the first experimental evidence for the oxidative addition of Rh(I) complex to a bicyclo<2.1.0>pentane system.Treatment of 3 with 2 equiv of triphenylphosphine gives rise to the starting bicyclo<2.1.0>pentane (1), instead of a keto compound.This contrasts markedly with reactions of acylrhodium complexes derived from other strained systems with triphenylphosphine to yield ketones.The structure of 3 is further confirmed by hydride reduction of 3 affording exo-3-(hydroxymethyl)noriceane (8), along with a small amount of two hydrocarbons, noriceane (9) and exo-3-methylnoriceane (10).