Photochemical reactivity of keto amidines. Type I rearrangement to aminocyclopropyl isocyanates and photochemical generation of bisisocyanates from …

BJ Swanson, GC Crockett, TH Koch

Index: Swanson, Barry J.; Crockett, Geoffrey C.; Koch, Tad H. Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1082 - 1086

Full Text: HTML

Citation Number: 7

Abstract

We have previously described the Norrish Type I rearrangement of 2-ethoxypyrrolin-5-ones to ethoxycyclopropyl isocyanates.'The reaction displays a high degree of stereospecificity2 and can be used as a synthetic method for the preparation of bicyclo [nlO] system^.^ The ethoxycyclopropyl isocyanate is potentially a synthetically useful structural unit. It is a cyclopropanone equivalent and has been used in the synthesis of the natural product~ ...