74502-16-2Relevant academic research and scientific papers
N-Heterocyclic carbene-catalyzed oxidations
Maki, Brooks E.,Chan, Audrey,Phillips, Eric M.,Scheidt, Karl A.
experimental part, p. 3102 - 3109 (2009/09/05)
N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.
Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes
Dambacher, Jesse,Zhao, Wen,El-Batta, Amer,Anness, Robert,Jiang, Changchun,Bergdahl, Mikael
, p. 4473 - 4477 (2007/10/03)
Water is demonstrated to be an excellent medium for the Wittig reaction employing stabilized ylides and aldehydes. Although the solubility in water appears to be an unimportant characteristic in achieving good chemical yields and E/Z-ratios, the rate of W
Copper(I)-promoted dechlorinative Surzur-Tanner rearrangement of 2,2,2-trichloroethyl carboxylates
Ram, Ram N.,Meher, Nabin Kumar
, p. 145 - 147 (2007/10/03)
(Matrix presented) 2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.
