99747-75-8Relevant 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 (1995)
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.
Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides
Shirakawa, Eiji,Imazaki, Yusuke,Hayashi, Tamio
supporting information; experimental part, p. 5088 - 5090 (2009/12/08)
In the presence of a ruthenium catalyst, alkenyl triflates were found to be transformed to the corresponding bromides, chlorides and iodides simply by treatment with a lithium halide (1.2 equiv.). The Royal Society of Chemistry 2009.
A Regioselective Entry to Vinyllithiums from Unsymmetrical Ketones via Enol Triflates
Wulff, William D.,Peterson, Glen A.,Bauta, William E.,Chan, Kin-Shing,Faron, Katherine L.,et al.
, p. 277 - 279 (2007/10/02)
The first method for the regioselective preparation of either the "kinetic" or "thermodynamic" vinyllithium from an unsymmetrical ketone is described
