Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Versatile Synthesis of Four-, Five-, and Six-membered Cyclic Ketones Using Methyl Methylthiomethyl Sulfoxide
Katsuyuki OguraMitsuo YamashitaMichiyo SuzukiShigeko FurukawaGen-ichi Tsuchihashi
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1984 Volume 57 Issue 6 Pages 1637-1642

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Abstract

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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