The synthesis of dichlorodiazirine and the generation of dichlorocarbene: spectroscopy and structure of dichlorocarbene ylides

…, DH Ess, KN Houk, K Krogh-Jespersen

Index: Moss, Robert A.; Tian, Jingzhi; Sauers, Ronald R.; Ess, Daniel H.; Houk, Kendall N.; Krogh-Jespersen, Karsten Journal of the American Chemical Society, 2007 , vol. 129, # 16 p. 5167 - 5174

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Citation Number: 29

Abstract

Reaction of 2, 4-dinitrophenoxychlorodiazirine (13) with chloride ions affords dichlorodiazirine (4). Photolysis of 4 generates dichlorocarbene. In laser flash photolysis (LFP) experiments, CCl2 forms chromophoric ylides or oxides with pyridine, 2-picoline, thioanisole, and oxygen. Spectroscopic and computational studies of the ylides are reported. The UV spectrum of CCl2 in solution, however, is not observed. It appears possible that ...