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Sulfinyl halide groups occur when a sulfinyl functional group is singly bonded to a halogen atom. They have the general formula R-S(O)-X, where X is a halogen. The best known examples are sulfinyl chlorides, thermolabile, moisture-sensitive compounds, which are useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides and thiosulfinates.^[1]

Sulfinyl chlorides

Sulfinic acid chlorides, or sulfinyl chlorides, are sulfinyl halides with the general formula R-S(O)-Cl. Methanesulfinyl chloride, CH₃S(O)Cl, is prepared by chlorination of dimethyl disulfide in acetic anhydride at -10 to 0 °C.^[2]

These compounds react readily with nucleophiles like water, alcohols, amines, thiols, and Grignard reagents. If the nucleophile is water the product is a sulfinic acid, if it is an alcohol the product is a sulfinic ester, if it is a primary or secondary amine the product is a sulfinamide, if it is a thiol the product is a thiosulfinate, while if it is a Grignard reagent the product is a sulfoxide.

Treatment of alkanesulfinyl chlorides having α-hydrogens with tertiary amine bases gives thiocarbonyl S-oxides (sulfines) as isolable compounds. Thus, treatment of n-propanesulfinyl chloride with triethylamine gives syn-propanethial-S-oxide, the lachrymatory agent of the onion.^[3]

References

^ Braverman, S (2008). "Alkanesulfinyl Halides". Sci. Synth. 39: 188–196. ISBN 9781588905307. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ Douglass, I.B.; Norton, R.V. (1973). "Methanesulfinyl chloride". Organic Syntheses. Coll. Vol. 5: 709 Article.
^ Block E., Gillies J.Z., Gillies C.W., Bazzi A.A., Putman D., Revelle L.K., Wang D., Zhang X.; Gillies, Jennifer Z.; Gillies, Charles W.; Bazzi, Ali A.; Putman, David; Revelle, Larry K.; Wang, Dongyi; Zhang, Xing (1996). "Allium Chemistry: Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (E,Z)-Propanethial S-Oxide, the Lachrymatory Factor of the Onion (Allium cepa)". J. Am. Chem. Soc. 118 (32): 7492–7501 [doi=10.1021/ja960722j]. doi:10.1021/ja960722j.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1] Braverman, S (2008). "Alkanesulfinyl Halides". Sci. Synth. 39: 188–196. ISBN 9781588905307. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

[2] Douglass, I.B.; Norton, R.V. (1973). "Methanesulfinyl chloride". Organic Syntheses. Coll. Vol. 5: 709 Article.

[3] Block E., Gillies J.Z., Gillies C.W., Bazzi A.A., Putman D., Revelle L.K., Wang D., Zhang X.; Gillies, Jennifer Z.; Gillies, Charles W.; Bazzi, Ali A.; Putman, David; Revelle, Larry K.; Wang, Dongyi; Zhang, Xing (1996). "Allium Chemistry: Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (E,Z)-Propanethial S-Oxide, the Lachrymatory Factor of the Onion (Allium cepa)". J. Am. Chem. Soc. 118 (32): 7492–7501 [doi=10.1021/ja960722j]. doi:10.1021/ja960722j.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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