Skip to main content
Journal cover image

Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane

Publication ,  Journal Article
Baldwin, SW; Doll, RJ; Haut, SA
Published in: Journal of Organic Chemistry
August 1, 1974

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.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

August 1, 1974

Volume

39

Issue

16

Start / End Page

2470 / 2472

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Baldwin, S. W., Doll, R. J., & Haut, S. A. (1974). Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane. Journal of Organic Chemistry, 39(16), 2470–2472. https://doi.org/10.1021/jo00930a053
Baldwin, S. W., R. J. Doll, and S. A. Haut. “Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane.” Journal of Organic Chemistry 39, no. 16 (August 1, 1974): 2470–72. https://doi.org/10.1021/jo00930a053.
Baldwin SW, Doll RJ, Haut SA. Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane. Journal of Organic Chemistry. 1974 Aug 1;39(16):2470–2.
Baldwin, S. W., et al. “Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane.” Journal of Organic Chemistry, vol. 39, no. 16, Aug. 1974, pp. 2470–72. Scopus, doi:10.1021/jo00930a053.
Baldwin SW, Doll RJ, Haut SA. Selectivity in the Free-Radical Reduction of Lactones with Trichlorosilane. Journal of Organic Chemistry. 1974 Aug 1;39(16):2470–2472.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

August 1, 1974

Volume

39

Issue

16

Start / End Page

2470 / 2472

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry