Thiocarbonyl‐imide aus der Umsetzung von 2,2,4,4‐Tetramethyl‐3‐thioxocyclobutanon mit Aryl‐aziden

Abstract

Thiocarbonyl Imides from the Reaction of 2,2,4,4‐Tetramethyl‐3‐thioxocylobutanone and Aryl Azides Reaction of 2,2,4,4‐tetramethyl‐3‐thioxocylobutanone ( 6 ) and 4‐methoxyphenyl, phenyl, and 4‐nitrophenyl azide ( 7a–c , respectively), at 80°, leads to the 11‐aryl‐5,10‐dithia‐11‐azadispiro[3.1.3.2]undecane‐2,8‐diones 8a–c ( Scheme 3 ), respectively, in 67–83% yield. The structure of 8b has been established by X‐ray crystallography. The formation of the products may be explained via an intermediate thiocarbonyl imide of type D ( Scheme 4 ), generated by the 1,3‐dipolar cycloaddition of the aryl azide with the CS bond of 6 and elimination of N 2 .