92749-14-9Relevant academic research and scientific papers
A Versatile Synthesis of Four-, Five-, and Six-membered Cyclic Ketones Using Methyl Methylthiomethyl Sulfoxide
Ogura, K.,Yamashita, M.,Suzuki, M.,Furukawa, S.,Tsuchinashi, G.
, p. 1637 - 1642 (1984)
Cyclization of 1,n-dihaloalkanes 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 acidhydrolysis thus provides a new method for synthesizing four-, five-, and six-membered cycloalkanones.Several representative preparations, such as those of substituted cyclobutanones, 3-cyclopentanone, and tetrahydro-4-pyrone are described.
