METALATION REACTIONS .3. METALATION OF OCTADECYNOLS AND OCTADECYNYL METHYL ETHERS

Octadecynyl alcohols and methyl ethers were metalated with butyllithium in ether and yielded on carbonation mono- and diacids. The two carboxyls in the diacids were situated on the same carbon atom. The alcohols were metalated faster than the ethers. The composition of the products was determined. The proton abstraction from both propargylic positions proceeded to a similar extent. Carbonation was more pronounced at the initially sp-hybridized atoms. The distance from the functional group was of little influence on the protonation and carbonation reactions, except for the case when the triple bond was very near the functional group. © 1969, American Chemical Society. All rights reserved.