Highly effective catalytic methods for ylide generation from diazo compounds. Mechanism of the rhodium-and copper-catalyzed reactions with allylic compounds

MP Doyle, WH Tamblyn, V Bagheri

Index: Doyle, Michael P.; Tamblyn, William H.; Bagheri, Vahid Journal of Organic Chemistry, 1981 , vol. 46, p. 5094 - 5102

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Citation Number: 146

Abstract

The catalytic effectiveness of rhodium (I1) acetate and hexadecacarbonylhexarhodium for ylide generation in reactions of diazo compounds with allyl methyl sulfide, representative allylic tertiary amines, and allyl halides is described. Exclusive formation of products derived from the [2, 3] sigmatropic rearrangement of ylide intermediates generated from ethyl diazoacetate and allyl sulfides, amines, or iodides is observed. Cyclopropanation is ...