Tetrahedron Letters

Fragmentation of cyclopropylmethoxychlorocarbene: Formation of cyclopropylcarbinyl/chloride ion pairs

RA Moss, GJ Ho, BK Wilk

Index: Moss, Robert A.; Ho, Guo Jie; Wilk, Bogdan K. Tetrahedron Letters, 1989 , vol. 30, # 19 p. 2473 - 2476

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Citation Number: 24

Abstract

Abstract The decomposition of cyclopropylmethyloxychlorodiazirine in MeCN proceeds via N 2 and CO loss, mainly to tight cyclopropylcarbinyl cation-chloride anion pairs that collapse to C 4 chlorides with substantial skeletal and label retention; the ion pairs can be intercepted by ethanol with less skeletal retention.