A Versatile Synthesis of Four-, Five-, and Six-membered Cyclic Ketones Using Methyl Methylthiomethyl Sulfoxide

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 a...

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Published inBulletin of the Chemical Society of Japan Vol. 57; no. 6; pp. 1637 - 1642
Main Authors Ogura, Katsuyuki, Yamashita, Mitsuo, Suzuki, Michiyo, Furukawa, Shigeko, Tsuchihashi, Gen-ichi
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.06.1984
Chemical Society of Japan
Subjects
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Hydrolysis
Sulfides
Thioacetal oxide
Dithioacetal
Cyclization
Aliphatic compound
Sulfoxide
Ketone
Halocarbon
Monocyclic compound
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Summary: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.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.57.1637