41068-60-4Relevant articles and documents
Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogues of tetracyanoquinodimethane
Rule,Detty,Kaeding,Sinicropi
, p. 1665 - 1673 (2007/10/02)
Synthetic routes to the unsubstituted 4H-thiopynan-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation of 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.
Chemistry of 1,1-Dioxothiopyrans. 1. Syntheses and Reactions of 2,6-Diphenyl-4H-thiopyran-4-one 1,1-Dioxide and 4H-Thioflaven-4-one, 1,1-Dioxide
Chen, Chin H.,Reynolds, George A.,Luss, H. R.,Perlstein, Jerome H.
, p. 3282 - 3289 (2007/10/02)
Improved syntheses and certain reactions of 2,6-diphenyl-4H-thiopyran-4-one 1,1-dioxide and 4H-thioflaven-4-one 1,1-dioxide are reported.Many of these derivatives, which display reversible, one-electron reduction waves in their cyclic voltammograms betwee