Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3,xH20. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic (-0 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' Et20, currently used to effect epoxide rearrangements.
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3oxH20. 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.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
A Facile and Efficient Method for the Rearrangement of Aryl-Substituted Epoxides to Aldehydes and Ketones Using Bismuth Triflate.-The title reaction is regioselective with aryl-substituted epoxides and the products arise from cleavage of the benzylic C-O bond. -(BHATIA, KAUSHIK A.; EASH, KYLE J.; LEONARD, NICHOLAS M.; OSWALD, MATTHEW C.; MOHAN, RAM S.; Tetrahedron Lett. 42 (2001) 46, 8129-8132; Dep. Chem., Ill. Wesleyan Univ., Bloomington, IL 61701, USA; EN)
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.