Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions

Authors
Crotti, P Di Bussolo, V Favero, L Pineschi, M Marianucci, F Renzi, G Amici, G Roselli, G
Citation
P. Crotti et al., Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions, TETRAHEDRON, 56(38), 2000, pp. 7513-7524
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
38
Year of publication
2000
Pages
7513 - 7524
Database
ISI
SICI code
0040-4020(20000915)56:38<7513:RCOTRO>2.0.ZU;2-D
Abstract
The regiochemical behavior of cyclohexene oxides bearing a remote O-functio nality was determined in the gas-phase in opening reactions with MeOH, usin g a gaseous acid (D-3(+), CnH5+, Me2F+) as the promoting agent. The results obtained indicate the incursion in the opening process in the gas phase of H+ (or D+)-mediated chelated bidentate species completely absent in the co rresponding reactions (methanolysis) carried out in the condensed phase. (C ) 2000 Elsevier Science Ltd. All rights reserved.