Tetrahedron p. 7077 - 7084 (1995)
Update date:2022-09-26
Topics:
Martinez, A. Garcia
Alvarez, R. Martinez
Vilar E. Teso
Fraile, A. Garcia
Barcina, J. Osio
Subramanian, L. R.
The solvolysis of 7,7-bis(trifluoromethylsulfonyloxy)-2-norbornene (1a), 1-trifluoromethylsulfonyloxy-1-phenylethylene (2a), 2-methyl-1-cyclohexen-1-yl triflate (3a) and 4-camphenyl triflate (4a) in carbon disulfide or diethyl ether with added MgI2 and MgBr2 yields a mixture of the corresponding halides 5b-e, 6b-c, 7b-c and 8b-c.The ionization of the triflate group is favoured by coordination with the magnesium halide.The reaction with MgI2 was found to be second-order and is about 50 times more reactive than MgBr2.The selectivities of the intermediate cations 5-8 toward the nucleophiles MgI2 and MgBr2 are nearly constant, although the solvolysis rates differ by more than three powers of ten.A theoretical explanation of the constant selectivity principle is given.
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