The regiochemical behavior of pairs of regio- and diastereoisomeric epoxides derived from the 3,4,5,6-tetrahydro-2H-pyrane system, bearing an acetal group as the remote functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+), as the promoting agent. With only one exception, the results obtained in the opening process of these epoxides indicate the incursion in the gas-phase of D+-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in the cd-phase.
|Autori interni:||CROTTI, PAOLO|
DI BUSSOLO, VALERIA
|Autori:||P. CROTTI; G. RENZI; FAVERO L; G. ROSELLI; V. DI BUSSOLO; M. CASELLI|
|Titolo:||Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions|
|Anno del prodotto:||2003|
|Digital Object Identifier (DOI):||10.1016/S0040-4020(03)00078-4|
|Appare nelle tipologie:||1.1 Articolo in rivista|