ARENE HYDRIDES - 7. REACTIONS OF ANTHRACENE HYDRIDE WITH STYRENE AND STILBENE OXIDE. REDUCTION IN BENZYLIC POSITION VIA NUCLEOPHILIC SUBSTITUTION

Article abstract of DOI:10.1016/S0040-4020(01)80088-0

Nucleophilic ring opening of oxiranes 1 and 2 by the carbanion AH(1-) ("anthracene hydride") proceeds rapidly giving rise to two isomeric products 3 and 5 from styrene oxide 1.In prolonged reactions, products with a 9-benzyl 9,10-dihydroanthracene structure (5, 6) are fragmented by an excess of carbanion to yield anthracene A and benzylic anions.The respective products 7 and 8 of reductive opening can be isolated in good yields with Na(1+) as gegen ion; however, they are transformed into styrenes with Li(1+).No fragmentation was observed in reactions of styrene oxide with xanthenyl anion Xan(1-).