Carbene reactions with cis azo functions. Formation of ester azines from. DELTA. 3-1, 3, 4-oxadiazolines

D Keus, M Kaminski, J Warkentin

Index: Keus, Diane; Kaminski, Maciej; Warkentin, John Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 343 - 347

Full Text: HTML

Citation Number: 26

Abstract

Thermolysis of a 2-alkoxy-2, 5, 5-trialkyl-A3-1, 3, 4-oxadiazoline (l), either neat or in a solvent such as benzene, leads to a carbonyl ylide intermediate which fragments to carbonyl compounds and carbenes. The latter attack the parent oxadiazoline at the azo function, presumably to form azomethine imine ylides. The latter ylides then fragment to form carbonyl compounds and azines such as R1 (R20) C= NN= C (OR2) R1, R1 (R20) C= NN= C (R3) ...