Synthesis and mechanistic study of fused 2-pyrrolines via thermolysis of 6-substituted-3,5-hexadienyl azidoformates |
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Authors: | Wu P L Chung T H Chou Y |
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Affiliation: | Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 701, Republic of China. wupl@mail.ncku.edu.tw |
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Abstract: | Thermolysis of 3,5-hexadienyl azidoformates at 300 degrees C, 0.05 Torr, led to a fused 2-pyrroline regiospecifically, 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 controlled 2-pyrroline with cis configuration between H-1 and H-8a whereas 6-substituted-3,5(Z)-hexadienyl azidoformates produced a cis and trans mixture. The mechanism was proposed as the loss of nitrogen to form an acyl nitrene, then addition to a double bond to produce an aziridine. Finally the cleavage of the C-C bond generated a vinylazomethine ylide followed by recyclization to a fused 2-pyrroline. |
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