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Title: Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters

Abstract

Primary alcohols can be deoxygenated cleanly and in high yield by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it both simple and convenient.

Authors:
 [1];  [2]
  1. Univ. of Illinois, Chicago, IL (United States). Dept. of Chemistry
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Biosciences Division; Univ. of Tennessee, Knoxville, TN (United States). Dept. of Biochemistry and Cellular & Molecular Biology
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE; Work for Others (WFO)
OSTI Identifier:
1327565
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Journal of Organic Chemistry
Additional Journal Information:
Journal Volume: 81; Journal ID: ISSN 0022-3263
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; deoxygenation; phosphorus chemistry; green chemistry; reduction; organic synthesis

Citation Formats

Chowdhury, Sarwat, and Standaert, Robert F. Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters. United States: N. p., 2016. Web. doi:10.1021/acs.joc.6b01699.
Chowdhury, Sarwat, & Standaert, Robert F. Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters. United States. doi:10.1021/acs.joc.6b01699.
Chowdhury, Sarwat, and Standaert, Robert F. Thu . "Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters". United States. doi:10.1021/acs.joc.6b01699. https://www.osti.gov/servlets/purl/1327565.
@article{osti_1327565,
title = {Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters},
author = {Chowdhury, Sarwat and Standaert, Robert F.},
abstractNote = {Primary alcohols can be deoxygenated cleanly and in high yield by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it both simple and convenient.},
doi = {10.1021/acs.joc.6b01699},
journal = {Journal of Organic Chemistry},
number = ,
volume = 81,
place = {United States},
year = {Thu Sep 15 00:00:00 EDT 2016},
month = {Thu Sep 15 00:00:00 EDT 2016}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

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Cited by: 1 work
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