Preparation of Isocyanates from Primary Amines and Carbon Dioxide Using Mitsunobu Chemistry1

…, MJ Horvath, PS Elmes, WR Jackson…

Index: Saylik, Dilek; Horvath, Michael J.; Elmes, Patricia S.; Jackson, W. Roy; Lovel, Craig G.; Moody, Keith Journal of Organic Chemistry, 1999 , vol. 64, # 11 p. 3940 - 3946

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Citation Number: 52

Abstract

Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at-78° C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates ...