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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Pyridinium ylids in synthesis. I. Alkylation of ylids and synthesis of ketones and acids

CA Henrick, E Ritchie and WC Taylor

Australian Journal of Chemistry 20(11) 2441 - 2453
Published: 1967

Abstract

Ylids generated by bases from pyridinium salts containing an activated methylene group can be C-alkylated in aprotic solvents. Reductive cleavage of the pyridine residue then affords alkylated ketones or esters. The reaction sequence constitutes an overall synthesis which is formally analogous to syntheses from β-keto esters.    Alkylation of N-pyridinium phenacylid with phenacyl bromide gave chiefly 1,2,3-tribenzoylpropene, the tautomerism of which was examined.

https://doi.org/10.1071/CH9672441

© CSIRO 1967

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