1984 Volume 57 Issue 6 Pages 1637-1642
Cyclization of 1,n-dihalo[or bis(tosyloxy)]alkanes with methyl methylthiomethyl sulfoxide in the presence of a base (n-BuLi or KH) gave three-, four-, five-, and six-membered 1-methylsulfinyl-1-methylthiocycloalkanes. These cyclization products were easily converted to the corresponding ketones by acid hydrolysis except 1-methylsulfinyl-1-methylthiocyclopropane which afforded a complicated mixture. The combination of the cyclization with the acid hydrolysis thus provides a new method for synthesizing four-, five-, and six-membered cycloalkanones. Several representative preparations, such as those of substituted cyclobutanones, 3-cyclopentenone, and tetrahydro-4-pyrone, are described.
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