π-Facial stereoselectivity in the Diels-Alder reactions of benzene oxides

JR Gillard, MJ Newlands, JN Bridson…

Index: Gillard, James R.; Newlands, Michael J.; Bridson, John N.; Burnell, D. Jean Canadian Journal of Chemistry, 1991 , vol. 69, # 9 p. 1337 - 1343

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Citation Number: 54

Abstract

The Diels-Alder reactions of N-phenylmaleimide and dimethyl acetylenedicarboxylate with benzene oxide (1, 3, 5-cyclohexatriene 1, 2-oxide, 3) and its more substituted derivatives 1, 2-dimethyl-1, 3, 5-cyclohexatriene 1, 2-oxide (7) and 10-oxatricyclo [4.3. 1.0] deca-2, 4-diene (11) in a kinetic manner gave exclusively products of addition anti to the plane- nonsymmetrical oxygen. The structures of the adducts were determined unequivocally by ...