The effect of the aromatic ring substituents on the product distribution of the gas-phase acid-induced ring opening of benzocondensed epoxides 2a and 2b with MeOH was examined and compared with results from methanolysis. The observed syn/anti diastereoselectivity is strictly dependent on the type of the aromatic ring substituent (6-OCH3 or 7-Br), and a very satisfactory Hammett-type linear correlation was found for both epoxides. A razionalization of the results is given.

AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE GAS-PHASE ACID-INDUCED RING-OPENING IN 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE

CROTTI, PAOLO;MINUTOLO, FILIPPO;
1993

Abstract

The effect of the aromatic ring substituents on the product distribution of the gas-phase acid-induced ring opening of benzocondensed epoxides 2a and 2b with MeOH was examined and compared with results from methanolysis. The observed syn/anti diastereoselectivity is strictly dependent on the type of the aromatic ring substituent (6-OCH3 or 7-Br), and a very satisfactory Hammett-type linear correlation was found for both epoxides. A razionalization of the results is given.
Chini, M; Crotti, Paolo; Minutolo, Filippo; Dezi, E; Lombardozzi, A; Pizzabiocca, A; Renzi, G.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/201675
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