13-Dithiolane-2-thiones

Ethynylquinoxaline (144) and bis(isopropoxythiocarbonyl) disulfide (145) gave 2-(2-oxo-l,3-dithiol-3-yl)quinoxaline (146) [l,l -azo(cyclohexanecar-bonitrile), PhMe, reflux, N2, 7 h 77%] 555 somewhat similarly, 2-(acetylethy-nyl)quinoxaline and 4-phenyl-1,3-dithiolane-2-thione gave 2-(5-acetyl-2-thioxo-l,3-dithiol-4-yl)quinoxaline (neat, 150°C, N2, 35 min 94%).1050... 

Ueno and Okawara (184) were the first to explicitly formulate a conjugated thiocarbonyl ylide as an intermediate in the reaction of 1,3-dithiolane-2-thione with 4-bromophenacyl bromide. The initially formed thiocarbonyl ylide undergoes deprotonation with sodium hydride to give 2-(4-bromophenyl)-l-oxa-4,6,9-trithias-piro[4.4]non-2-ene. 1,3-Diacylated thiocarbonyl ylides of type 149 (Scheme 5.45) have also been proposed as intermediates in the reaction of 1,3-diphenylpropane-1,3-dione with thionyl chloride. This reaction leads to 2,2,4-tribenzoyl-5-phenyl-... 

The 8 + 2-cycloaddition of 2//-cy c I o h cpta[h ] furan -2 - one (155) with acyclic 1,3-dienes provides a facile route to bicyclo[5.3.0] ring systems (156) (Scheme 61).291 2H-Benzo[Z>]thiete in the o-quinoid form undergoes 8 + 2-cycloaddition with 1,3-dithiolane-2-thione, l,3-dithiole-2-thiones, and adamantanethione to produce 4//-1,3-benzoditliianes.292... 

Allyl-/-butyltrithiocarbonates (236), which are obtained from readily available allyl halides by a multi-step reaction with sodium t-butyltrithiocarbonates, can be cyclized with concomitant loss of hydrogen iodide and isobutylene using elemental iodine to afford 1,3-dithiolane-2-thiones (237) ( heme 48) treatment of (237) with pyridine again results in a loss of hydrogen iodide and (238) is formed. Compound (238) can be isomerized using trifluoroacetic acid and (239) is obtained <80JOC2959>. 

Dithiolane 1,3-Dithiolane 1,3-Dithiolane-2-thione Ditliopyr Dithizone... 

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