Spectroscopic detection of an arylchlorocarbene-ethyl acetate carbonyl ylide and subsequent oxirane formation

JE Chateauneuf, MTH Liu

文献索引：Chateauneuf, John E.; Liu, Michael T. H. Journal of the American Chemical Society, 1991 , vol. 113, # 17 p. 6585 - 6588

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被引用次数: 21

摘要

Abstract: Laser flash photolysis of 3-chloro-3-@-nitrophenyl) diazirine (1) generates the corresponding ground-state singlet carbene (Am,= 310 nm), which reacts with ethyl acetate to form a carbonyl ylide of the ester (A,= 490 nm). The absolute rate constant for ylide formation in CH2CI2 is k=(2.85 f 0.17) X lo6 MI sl. Subsequent cyclization of the ylide to the corresponding oxirane (A,= 350 nm) occurs with a rate constant of 1.26 X lo6 sI (21" C) in ...