Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide


Journal Article

The cleavage of various cyclic ethers (3- to 7-membered rings) was achieved under very mild conditions using dimethylboron bromide to afford the corresponding bromo alcohols. In particular, 2-substituted tetrahydrofurans were regioselectively cleaved by a predominantly SN2-type mechanism favoring the formation of primary vs. secondary bromides. Dimethylboron bromide also cleaved chemoselectively substituted tetrahydrofurans in the presence of functional groups such as acyclic ethers, silyl ethers, esters, amides, ketones, etc. © 1987, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Guindon, Y; Therien, M; Girard, Y; Yoakim, C

Published Date

  • May 1, 1987

Published In

Volume / Issue

  • 52 / 9

Start / End Page

  • 1680 - 1686

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00385a007

Citation Source

  • Scopus