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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

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

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被引用次数: 146

摘要

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 ...