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Direct conversion of benzylic and allylic alcohols to phosphonates.

ABSTRACT: Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2).

SUBMITTER: Barney RJ

PROVIDER: S-EPMC3204863 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Direct conversion of benzylic and allylic alcohols to phosphonates.

Barney Rocky J RJ Richardson Rebekah M RM Wiemer David F DF

The Journal of organic chemistry 20110315 8

Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2). ...[more]

PMID: 21405073

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