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A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
Scholarship
Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C―O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
Scholarship
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3•xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Scholarship
Ketoximes undergo facile deprotection in acetone-H20 (9: 1) in the presence 01' 0.5 equivalents of Bi(N03h•5H20. Bismuth(III) nitrate is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively nontoxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.