Dienediolates of unsaturated carboxylic acis in synthesis: Aldehydes and ketones from alkyl halides, by ozonolysis of beta,gamma-unsaturated alpha-Alkyl carboxylic acids: The role of a tertiary amine in the cleavage of ozonides

Aurell, M.-Jose; Ceita, L.; Mestres, R.; Tortajada, A.

Tetrahedron 53(31): 10883-10898


ISSN/ISBN: 0040-4020
Accession: 008463298

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A convenient two-step procedure for a two carbon homologative conversion of alkyl halides into aldehydes and methyl ketones by alpha-alkylation of unsaturated carboxylic acids, followed by ozonolysis is developed and applied to the synthesis of omega-chloro aldehydes. Triethylamine is superior to dimethyl sulfide or triphenylphosphine for cleavage of the ozonides, except when aldol condensation side reactions require use of protic solvents and iodide salts. Cleavage of the ozonides by triethylamine is shown to occur mainly through a reductive process.