Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates
A method for regio- and stereoselective anti-addition of the perfluoroalkyl and the triflate group of phenyl(perfluoroalkyl)iodonium triflates to alkynes is presented. The radical reaction uses cheap CuCl as a smart initiator and can be conducted in gram scale. The perfluoroalkyltriflated products are readily further functionalized, rendering this transformation valuable.
Thermal Reaction of Ethynylphthalimides and Hydration of N-(4-Ethynylphenyl)phthalimide
Three ethynyl substituted phenylphthalimides were prepared and characterized by high pressure liquid chromatography, differential scanning calorimetry, and mass spectroscopy.When the preparation of N-(4-ethynylphenyl)phthalimide was attempted by the thermal cyclodehydration of N-(4-ethynylphenyl)-2-carboxybenzamide, N-(4-acetylphenyl)phthalimide was obtained as the major component.This unusual hydration of an ethynyl group was investigated and a mechanism was proposed to explain it.
Hergenrother, P. M.
p. 5 - 10
(2007/10/02)
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