ChemInform Abstract: Synthesis and Mechanistic Study of Fused 2‐Pyrrolines via Thermolysis of 6‐Substituted‐3,5‐hexadienyl Azidoformates.

Abstract

Synthesis and Mechanistic Study of Fused 2-Pyrrolines via Thermolysis of 6-Substituted-3,5-hexadienyl Azidoformates.-Heating of dienyl azidoformates at 300 • C, 0.05 Torr provides a new regioselective approach to fused 2-pyrrolines. It proceeds via formation of acyl nitrenes and aziridines, C-C bond cleavage, and recyclization to fused 2-pyrrolines. The reaction outcome depends on the configuration of the C5-C6 double bond, whereas the configuration of the C3-C4 double bond has no effect on the outcome. -