40648-08-6Relevant academic research and scientific papers
Selectivity in the Reactions of Less Stable Carbocations with Magnesium Halides in Aprotic Solvents. A Theoretical Approach to the Constant Selectivity Principle.
Martinez, A. Garcia,Alvarez, R. Martinez,Vilar E. Teso,Fraile, A. Garcia,Barcina, J. Osio,Subramanian, L. R.
, p. 7077 - 7084 (2007/10/02)
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.
The Reaction of Vinyl Phosphates with Iodotrimethylsilane: Synthesis of Vinyl Iodides from Ketones
Lee, Koo,Wiemer, David F.
, p. 2433 - 2436 (2007/10/02)
A new method for preparation of vinyl iodides from ketones is described, based on the reaction of vinyl phosphates with iodotrimethylsilane.
Herstellung von Vinyl-iodiden durch Umsetzung von Vinyl-triflaten mit Magnesiumiodid
Garcia Martinez, A.,Martinez Alvarez, R.,Garcia Fraile, A.,Subramanian, L. R.,Hanack, Michael
, p. 222 - 224 (2007/10/02)
The reaction of vinyl trifluoromethanesulfonates (triflates) with anhydrous magnesium iodide in the presence of triethylamine in carbon disulfide or cyclohexane gives vinyl iodides in good yields.No reaction is observed with phenyl and cyclopentenyl trifl
