The regioselectivity of the addition reaction of MeOH both in the condensed (MeOH/H2SO4) and in the gas-phase (MeOH/D3+) was examined in a series of activated aziridines. The results indicate that gas-phase operating conditions are particularly favorable for the occurrence of D+-mediated chelated bidentate species which influence the regioselectivity of the opening process. In the condensed phase, the chelating MeOH/LiClO4 protocol turned out to be decidedly less effective for regioselectivity and also in determining the composition of the reaction mixture.
|Autori:||P. CROTTI; V. DI BUSSOLO; G. RENZI; G. ROSELLI; S. GIULI; S. TSITSIGIA; M. R. ROMANO|
|Titolo:||Regiochemical Control of the ring-opening of aziridines by means of chelating processes. Part 4.: Regioselectivity of the opening reactions with MeOH of 1-(benzyloxy)-2,3- and -3,4-N-(methoxycarbonyl)aziridoalkanes under condensed and gas-phase operating conditions|
|Anno del prodotto:||2007|
|Digital Object Identifier (DOI):||10.1016/j.tet.2007.04.040|
|Appare nelle tipologie:||1.1 Articolo in rivista|