Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane

Journal Article (Journal Article)

Each of the generally recognized methods for converting lactones to cyclic ethers suffers from distinct structural limitations. For instance, Adams catalyst in an acidic medium will reduce δ-lactones to the corresponding ethers but fails completely with γ- and ε-lactones.2 Pettit's reagents derived from complex metal hydrides and boron trifluoride are very effective when the alcohol portion of the lactone is tertiary, but the yields of ethers decrease dramatically as substitution at the alcohol portion is decreased.3 Published results suggest a further limitation to the Pettit procedure when the lactone is part of an otherwise flexible system that can adopt a more favorable conformation by ring opening. For instance, Bruice4 has reported that no ether is formed on reduction of 2-oxabicyclo[ 2.2.2]octan-3-one (1) with BF3-B2H6 and we have encountered a similar failure with 6-oxabicyclo[3.2.1 Joctan-7-one (2). © 1974, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; Doll, RJ; Haut, SA

Published Date

  • August 1, 1974

Published In

Volume / Issue

  • 39 / 16

Start / End Page

  • 2470 - 2472

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00930a053

Citation Source

  • Scopus