Strained organic molecules. II. Rearrangements of 1-(1,2,3-triphenylcycloprop-2-enyl)-3-diazopropan-2-one (1,2,-3-triphenylcycloprop-2-enyl)acetyl azide

Abstract

Several reactions are discussed. In the presence of silver benzoate, triethylamine, and ethanol, 1-( 1,2,3-triphenylcycloprop-2-enyl)-3-diazopropan-2-one ( 1 b) rearranges to two isomers of ethyl ( 1,2-diphenylcyclobut-2-eny1)phenylacetate (6a and b). Thermally, (1,2,3-triphenylcycloprop-2-enyl)acetyl azide (8b) rearranges to the corresponding isocyanate which was trapped with either dimethylamine or ethanol. With ultraviolet light the azide follows a different pathway.