The Role of Hydrogen Bonding in the Intramolecular Cyclization of Carbenes

David W. Jeffery, Troy Lister and Rolf H. Prager

Abstract

The cyclization products from the photolysis of 3-arylamino-4-ethoxycarbonyl-2-heteroarylisoxazol-5(2H)-ones are interpreted as arising from intramolecular cyclization of carbenes. The mode of cyclization appears to be controlled by hydrogen bonding of the 3-NH group with either the 2-heteroaryl group or the 4-ethoxycarbonyl group.

Australian Journal of Chemistry 57(5) 491 - 496 (2004) doi:10.1071/CH03139