Convenient syntheses of bifunctional C12-acyclic compounds from cyclododecanone
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1369-1372
- https://doi.org/10.1039/p19830001369
Abstract
The conversion of cyclododecanone by convenient, non-hazardous, and high-yielding reactions into a set of useful C12-bifunctional intermediates is described. Baeyer–Villiger oxidation and hydrolysis give a hydroxy acid, successively converted into the bromo acid, bromo alcohol, crude bromo aldehyde, pure bromo aldehyde ethylene acetal, and pure bromo aldehyde. Preferred reagents for the transformation CO2H → CHO are borane–dimethyl sulphide followed by dimethyl sulphoxide–oxalyl dichloride–triethylamine.Keywords
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