Tetrahedron

Selectivity in the reactions of less stable carbocations with magnesium halides in aprotic solvents. A theoretical approach to the constant selectivity principle

…, ET Vilar, AG Fraile, JO Barcina, LR Subramanian

Index: Martinez, A. Garcia; Alvarez, R. Martinez; Vilar E. Teso; Fraile, A. Garcia; Barcina, J. Osio; Subramanian, L. R. Tetrahedron, 1995 , vol. 51, # 25 p. 7077 - 7084

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Citation Number: 2

Abstract

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 halides. The reaction with ...