1,3,5-Trithiane | Wikipedia audio article
Channel: wikipedia tts
Date: 25/12/2018

This is an audio version of the Wikipedia Article:
https://en.wikipedia.org/wiki/1,3,5-Trithiane


00:01:20 Trithianes



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SUMMARY
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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.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.
(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:
(CH2S)3  +  9 Cl2  +  6 H2O   →   3 ClCH2SO2Cl  +  12 HCl