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|Section2= |Section3= }} 1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.〔Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://orgsyn.org/Content/pdfs/procedures/CV2P0610.pdf〕 Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.〔Seebach, D.; Beck, A. K. “Aldehydes From ''sym''-Ttrithiane: ''n''-Pentadecanal” Organic Syntheses, Collected Volume 6, p.869 (1988). http://orgsyn.org/Content/pdfs/procedures/CV6P0869.pdf〕 :(CH2S)3 + RLi → (CH2S)2(CHLiS) + RH :(CH2S)2(CHLiS) + R’Br → (CH2S)2(CHR’S) + LiBr :(CH2S)2(CHR’S) + H2O → R’CHO + …. Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above. It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:〔Paquette, L. A.; Wittenbrook, L. S. “2-Chlorothiirane 1,1-Dioxide” Organic Syntheses, Collected Volume 5, p.231 (1973). http://orgsyn.org/Content/pdfs/procedures/CV5P0231.pdf〕 :(CH2S)3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl ==Trithianes== Trithiane is the parent of a class of heterocycles called trithianes. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes suffer trimerization. The reaction is reversed thermally. : 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「1,3,5-Trithiane」の詳細全文を読む スポンサード リンク
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