Journal of Organic Chemistry p. 3790 - 3792 (1989)
Update date:2022-07-29
Topics:
Maryanoff, Cynthia A.
Karash, Carole B.
Turchi, Ignatius J.
Corey, Eugene R.
Maryanoff, Bruce E.
Reaction of 1 and 2 in acetic anhydride at 110 deg C produced intermediate 6, which captured the exo stereochemistry of the unseen primary cycloadduct, 5.Thermolysis of 6 at a much higher temperature readily gave the expected dihydroazepine 4.The stereochemistry of 6 was unambiguously established by the single-crystal X-ray analysis of methyl ester 8, formed by treating 6 with diazomethane under mild conditions.The isolation of 6 suggests that elimination of carbon dioxide from such primary cycloadducts need not be a concerted process.
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