AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE CONDENSED-PHASE 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

Authors
CROTTI P DIBUSSOLO V FAVERO L PINESCHI M SERGIAMPIETRI D RENZI G RICCIUTELLI M ROSELLI G
Citation
P. Crotti et al., AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE CONDENSED-PHASE 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, Tetrahedron, 53(15), 1997, pp. 5515-5536
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
15
Year of publication
1997
Pages
5515 - 5536
Database
ISI
SICI code
0040-4020(1997)53:15<5515:ASEOTS>2.0.ZU;2-Z
Abstract
The ring-opening reactions with MeOH of the title benzocondensed 2-ary l 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 li near correlation. Results indicate that the secondary or tertiary natu re of the benzylic oxirane carbon is not responsible for the different stereochemical behavior so far encountered in different 2-aryl oxiran e systems under the same operating conditions. (C) 1997 Elsevier Scien ce Ltd.