Twin annulation of naphthalene via a 1, 5-naphthodiyne synthon. New syntheses of chrysene and dibenzo [b, k] chrysene
CS LeHoullier, GW Gribble
Index: LeHoullier, Craig S.; Gribble, Gordon W. Journal of Organic Chemistry, 1983 , vol. 48, # 10 p. 1682 - 1685
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Citation Number: 41
Abstract
New, efficient syntheses of chrysene (l), dibenzo [b, k] chrysene (16), and derivatives are described that feature, as the key step, the formal cycloaddition between 1, 5naphthodiyne (3) and a heterocyclic diene (furan, pyrroles, isoindoles). Subsequent manipulation affords the arene in 26-49% overall yield from comhercially available 2, 6-dibromo-l, 5dihydroxynaphthalene (5). The latter is easily converted to ditosylate 6, which, with ...
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