A versatile synthesis of four-, five-, and six-membered cyclic ketones using methyl methylthiomethyl sulfoxide.

K Ogura, M Yamashita, M Suzuki, S Furukawa…

Index: Ogura, K.; Yamashita, M.; Suzuki, M.; Furukawa, S.; Tsuchinashi, G. Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 6 p. 1637 - 1642

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Citation Number: 23

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 ...