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- W190035770 abstract "Abstract Thiols add readily and reversibly to the carbonyl group of aldehydes or ketones to form the hemimercaptals. Hemimercaptals are ordinarily unstable, but can be isolated in certain cases. Under acid catalysis, they commonly react with a second molecule of thiol to produce mercaptals. When an α-hydrogen atom is available on the carbonyl compound, and there is a proper balance of steric and electronic factors, the hemimercaptal may eliminate water to produce an unsaturated sulfide. Addition of 1,2- and 1,3-dithiols to carbonyl compounds leads to the formation of the heterocyclic 1,3-dithiolanes and 1,3-dithianes. Thioxolanes and oxythianes are likewise formed from hydroxythiols. When hydrogen sulfide is added to a carbonyl compound under acid conditions, the reactions follow the same course, but can be much more complicated by the possibility of further reaction of the intermediate hydroxythiols, gem-dithiols and vinyl thiols with the initial carbonyl compound or with themselves. Few examples of hydroxythiols are known, but gem-dithiols have recently been obtained. Hydroxythiols may be intermediates in the formation of trithianes, as well as thiones, when aldehydes and ketones are treated with hydrogen sulfide under acid conditions. The acid-catalyzed addition of hydrogen sulfide to certain ketones has led to the formation of doubly unsaturated sulfides, which undoubtedly arises from vinyl thiol intermediates." @default.
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- W190035770 date "1961-01-01" @default.
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- W190035770 title "ADDITION OF THIOLS OR HYDROGEN SULFIDE TO CARBONYL COMPOUNDS" @default.
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