The stereochemistry of the acid-induced ring opening reactions (hydrolysis, methanolysis and trichloroacetolysis) of 1,2-epoxides derived from ring-substituted 3,4-dihydronaphthalene has been examined. In every case, a satisfactory Hammett-type linear correlation was found between the diastereoselectivity of the reaction and the sigma+ constant of the aromatic substituent. The stereoselectivity of the opening reaction turned out to be largely driven by the reactive conformation of the epoxide and/or of the opening process intermediates.
AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE ACID-INDUCED RING-OPENING OF 1,2-EPOXIDES DERIVED FROM 3,4-DIHYDRONAPHTHALENE - IMPORTANCE OF THE REACTIVE CONFORMATIONS FOR THE STEREOSELECTIVITY
CROTTI, PAOLO;MINUTOLO, FILIPPO;MARTINELLI, ADRIANO;
1994-01-01
Abstract
The stereochemistry of the acid-induced ring opening reactions (hydrolysis, methanolysis and trichloroacetolysis) of 1,2-epoxides derived from ring-substituted 3,4-dihydronaphthalene has been examined. In every case, a satisfactory Hammett-type linear correlation was found between the diastereoselectivity of the reaction and the sigma+ constant of the aromatic substituent. The stereoselectivity of the opening reaction turned out to be largely driven by the reactive conformation of the epoxide and/or of the opening process intermediates.File in questo prodotto:
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