| Abstract
| - Thermolysis of 3,5-hexadienyl azidoformates at 300 °C, 0.05 Torr, led to a fused 2-pyrrolineregiospecifically, regardless of the configuration E or Z between the C-3 and C-4 double bond.Thermolysis of 6-substituted-3,5(E)-hexadienyl azidoformates yielded a kinetically controlled2-pyrroline with cis configuration between H-1 and H-8a whereas 6-substituted-3,5(Z)-hexadienylazidoformates produced a cis and trans mixture. The mechanism was proposed as the loss of nitrogento form an acyl nitrene, then addition to a double bond to produce an aziridine. Finally the cleavageof the C−C bond generated a vinylazomethine ylide followed by recyclization to a fused 2-pyrroline.
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