Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide
Publication
, Journal Article
Guindon, Y; Therien, M; Girard, Y; Yoakim, C
Published in: Journal of Organic Chemistry
May 1, 1987
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.
Duke Scholars
Altmetric Attention Stats
Dimensions Citation Stats
Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
May 1, 1987
Volume
52
Issue
9
Start / End Page
1680 / 1686
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Guindon, Y., Therien, M., Girard, Y., & Yoakim, C. (1987). Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide. Journal of Organic Chemistry, 52(9), 1680–1686. https://doi.org/10.1021/jo00385a007
Guindon, Y., M. Therien, Y. Girard, and C. Yoakim. “Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide.” Journal of Organic Chemistry 52, no. 9 (May 1, 1987): 1680–86. https://doi.org/10.1021/jo00385a007.
Guindon Y, Therien M, Girard Y, Yoakim C. Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide. Journal of Organic Chemistry. 1987 May 1;52(9):1680–6.
Guindon, Y., et al. “Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide.” Journal of Organic Chemistry, vol. 52, no. 9, May 1987, pp. 1680–86. Scopus, doi:10.1021/jo00385a007.
Guindon Y, Therien M, Girard Y, Yoakim C. Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide. Journal of Organic Chemistry. 1987 May 1;52(9):1680–1686.
Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
May 1, 1987
Volume
52
Issue
9
Start / End Page
1680 / 1686
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry