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.[3]
(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.
Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalentgroups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH2)n(SCHR)3-n.[5]
The conformation of trithianes has been well investigated.[6]
^Edema, Jilles J. H.; Hoogenraad, Marcel; Schoonbeek, Franck S.; Kellogg, Richard M.; Kooijman, Huub; Spek, Anthony L. (2010). "Alkylation of the SCS linkage. Towards lipophilic mono- and ditopic heavy-metal receptors containing trithiane building blocks. Molecular structure of cis-2,4,6-tribenzyl-1,3,5-trithiane". Recueil des Travaux Chimiques des Pays-Bas. 112 (6): 370–375. doi:10.1002/recl.19931120611.
^Breslow, David S.; Skolnik, Herman (2009). "C3S3 Ring Systems". Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2. Vol. 21. John Wiley & Sons. p. 689. ISBN978-0-470-18833-0.
