Aromatic substituent effect on the stereoselectivity of the condensed- and gas-Phase Acid-Induced methanolysis in 2-Aryloxiranes derived from 3,4-dihydronaphthalene and trans-1,2,3,4,4a,10a-Hexahydrophenanthrene bearing a tertiary benzylic oxirane nucleophilic centre

Article abstract of DOI:10.1016/S0040-4020(97)00209-3

The ring-opening reactions with MeOH of the title benzocondensed 2-aryl oxiranes 6 and 7a,b both in the condensed (methanolysis) and in the gas phase were examined, obtaining in all cases a good Hammett-type linear correlation. Results indicate that the secondary or tertiary nature of the benzylic oxirane carbon is not responsible for the different stereochemical behavior so far encountered in different 2-aryl oxirane systems under the same operating conditions.