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.

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

CROTTI, PAOLO;FAVERO, LUCILLA;DI BUSSOLO, VALERIA;
2003

Abstract

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.
Crotti, Paolo; G., Renzi; Favero, Lucilla; G., Roselli; DI BUSSOLO, Valeria; M., Caselli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/203840
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