Journal of Organic Chemistry p. 2665 - 2668 (1988)
Update date:2022-09-26
Topics:
Krow, Grant R.
Cannon, Kevin C.
Carey, James T.
Ma, Hong
Raghavachari, Ramesh
Szczepanski, Steven V.
Thermal rearrangements of N-acyl-7-aminocyclohepta-1,3,5-trienes 7b-e in octane or xylene provide <4+2>-cycloaddition products 8b-e and <1,5>-hydrogen sigmatropic rearrangement products 9b-e.The relative rate of formation for 8e/9e is 1.5 in refluxing octane.At a higher reaction temperature in xylene and longer reaction times, 7b afforded a second hydrogen-shift product 10b.No thermal <3,3>-carbon shift products were observed from N-allyl cycloheptatrienes 9b-e or 10b in octane or xylene.The thermal behavior of 7b-e can be contrasted with that of O-allyl cyclohepta-1,3,5-triene 1.
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