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
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
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
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