The Journal of organic chemistry

Remote electronic effects in the rhodium-catalyzed nucleophilic ring opening of oxabenzonorbornadienes

M Lautens, GA Schmid, A Chau

Index: Lautens, Mark; Schmid, Gavin A; Chau, Anh The Journal of organic chemistry, 2002 , vol. 67, # 23 p. 8043 - 8053

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Citation Number: 42

Abstract

We report the application of our rhodium-catalyzed nucleophilic ring-opening methodology to unsymmetrically arene-substituted oxabenzonorbornadienes. The regioselectivity of the ring opening was investigated using a variety of nucleophiles that led to a broad selection of dihydronaphthalene products. It was found that good to excellent regioselectivities are obtained using strongly π-donating substituents, whereas σ-donating and electron- ...