1,3,5-Trithiane

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 and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.^[2]

Product highlight

Precisely determine water content - easier than ever before

Mobile Raman spectrometer for real-time data analysis on site

Efficient inline analysis for liquids and solids

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 in turn 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.

It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethylsulfonyl chloride:^[4]

(CH₂S)₃ + 9 Cl₂ + 6 H₂O → 3 ClCH₂SO₂Cl + 12 HCl

References

1. ^ David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005.
2. ^ Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0610.pdf
3. ^ Seebach, D.; Beck, A. K. “Aldehydes From sym-Ttrithiane: n-Pentadecanal” Organic Syntheses, Collected Volume 6, p.869 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0869.pdf
4. ^ Paquette, L. A.; Wittenbrook, L. S. “2-Chlorothiirane 1,1-Dioxide” Organic Syntheses, Collected Volume 5, p.231 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0231.pdf