Irradiation of methyl diazomalonate in solution. Reactions of singlet and triplet carbenes with carbon-carbon double bonds

M Jones Jr, W Ando, ME Hendrick…

Index: Jones,M. et al. Journal of the American Chemical Society, 1972 , vol. 94, # 21 p. 7469 - 7479

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Citation Number: 77

Abstract

Abstract: Direct and sensitized irradiation of methyl diazomalonate gives singlet and triplet biscarbomethoxycarbene, respectively. The reactions of these species with carbon-carbon double bonds are described. Cyclopropanes are formed with substantial retention of stereochemistry from the singlet but with complete loss from the triplet. Additions to allene, norbornadiene, and benzene are also achieved. The reactions of several triplet carbenes ...