Journal of Organic Chemistry p. 4460 - 4462 (1984)
Update date:2022-07-30
Topics:
Yamaguchi, Ryohei
Kawanisi, Mituyosi
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).
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