Chemistry of sulphines. Part XVI. Aliphatic sulphines from non-enethiolisable thioketones and their cycloaddition reactions with diazoalkanes

Oxidation with peroxy-acid of the non-enethiolisable thioketones adamantanethione, 2,2,4,4-tetramethyl-3-thioxo-cyclobutanone and 2,2,4,4-tetramethylcyclobutane-1,3-dithione gives the corresponding sulphines in high yields. Cycloaddition reactions of these sulphines with 2-diazopropane lead to Δ3-1,3,4-thiadiazoline S-oxides; from diazomethane and 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-oxide an episulphoxide was isolated.