Journal of Organic Chemistry p. 1611 - 1616 (1985)
Update date:2022-08-03
Topics:
Gribble, Gordon W.
LeHoullier, Craig S.
Sibi, Mukund P.
Allen, Robert W.
The Diels-Alder reaction between isoindoles (7) and 1-naphthalyne, as generated from 1-bromo-2-fluoronaphthalene (11a), 1-bromo-2-iodonaphthalene (11b), or 1-bromo-2-naphthyl p-toluenesulfonate (11c), affords the corresponding 7,12-dihydrobenzanthracen-7,12-imine (17).Oxidative deamination of 17 with m-chloroperbenzoic acid gives the polyhalogenated benzanthracenes(3, 19a-d) in fair to good overall yields.A similar sequence with 7 and 5,6,7,8-tetrafluoro-1-naphthalyne, as generated from 1,2,3,4-tetrafluoro-5-chloronaphthalene (14a), 1,2,3,4-tetrafluoro-5-bromonaphthalene (14b), or 6-bromo-1,2,3,4-tetrafluoro- 5-naphthyl p-toluenesulfonate (16), gives, after deamination of the intermediate benzanthracenimine 18, benzanthracenes 5 and 19e in low overall yield.
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