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

Authors
CHINI M CROTTI P MINUTOLO F DEZI E LOMBARDOZZI A PIZZABIOCCA A RENZI G
Citation
M. Chini et al., AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE GAS-PHASEACID-INDUCED RING-OPENING IN 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE, Tetrahedron, 49(26), 1993, pp. 5845-5858
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
26
Year of publication
1993
Pages
5845 - 5858
Database
ISI
SICI code
0040-4020(1993)49:26<5845:ASEOTS>2.0.ZU;2-S
Abstract
The effect of the aromatic ring substituents on the product distributi on of the gas-phase acid-induced ring opening of benzocondensed epoxid es 2a and 2b with MeOH was examined and compared with results from met hanolysis. The observed syn/anti diastereoselectivity is strictly depe ndent on the type of the aromatic ring substituent (6-OCH3 or 7-Br), a nd a very satisfactory Hammett-type linear correlation was found for b oth epoxides. A razionalization of the results is given.