Tetrahedron p. 10115 - 10124 (1995)
Update date:2022-09-26
Topics:
Morrow, Gary W.
Marks, Tina M.
Sear, Debra L.
2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.
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Doi:10.1016/0040-4020(95)00686-3
(1995)Doi:10.1039/c9sc01574d
(2019)Doi:10.1021/ja00992a027
(1967)Doi:10.1021/jo01033a511
(1964)Doi:10.1039/c8ob00101d
(2018)Doi:10.1002/hlca.19950780721
(1995)
