Free radical addition of isobutyric acid to α,ω-diolefins. A new route to α,α,α′,α′-tetramethylalkanedioic acids
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 1655-1660
- https://doi.org/10.1039/p29730001655
Abstract
2,2,9,9-Tetramethylsebacic and 2,2,8,8-tetramethylazelaic acids have been synthesized in resonable yields (55% in the case of the former) by the free radical addition of isobutyric acid to hexa-1,5-diene and penta-1,4-diene respectively using di-t-butyl peroxide as initiator. Extension of this method to hepta-1,6-diene and octa-1,7-diene led to the production of new cyclic compounds. cis- and trans-2,2-Dimethyl-3-(2-methylcyclopentyl)propionic acids were obtained from hepta-1,6-diene and cis- and trans-2,2-dimethyl-3-(2-methylcyclohexyl)propionic acids and 2,2-dimethyl-3-cycloheptylpropionic acid from octa-1,7-diene. The mechanisms of these reactions are discussed. Some attempted additions of isobutyric acid to methylene cycloalkanes containing five-, six-, and seven-membered rings are described.Keywords
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