The ring-opening reactions with MeOH of the title benzocondensed 2-aryl oxiranes [I, II ,and III (R1,R2 given:H,Br;H,H;Me,H)] both in the condensed (methanolysis) and in the gas phase were examd., obtaining in all cases a good Hammett-Brown LFER. Results indicate that the secondary or tertiary nature of the benzylic oxirane carbon is not responsible for the different stereochem. behavior so far encountered in different 2-aryl oxirane systems under the same operating conditions.
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 center
CROTTI, PAOLO;DI BUSSOLO, VALERIA;FAVERO, LUCILLA;PINESCHI, MAURO;
1997-01-01
Abstract
The ring-opening reactions with MeOH of the title benzocondensed 2-aryl oxiranes [I, II ,and III (R1,R2 given:H,Br;H,H;Me,H)] both in the condensed (methanolysis) and in the gas phase were examd., obtaining in all cases a good Hammett-Brown LFER. Results indicate that the secondary or tertiary nature of the benzylic oxirane carbon is not responsible for the different stereochem. behavior so far encountered in different 2-aryl oxirane systems under the same operating conditions.File in questo prodotto:
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