ok, time for another _Organic Synthesis_ roulette
the word of the day: "smell" (really)
http://orgsyn.org/demo.aspx?prep=v94p0217
ok this is a somewhat fascinating but niche one. this article describes synthesis of a reagent for putting _trifluoromethylthio_ groups on things, so that's CF₃S-
not a group you see every day, but it's apparently useful in drug synthesis and other things where lipophilicity, i.e. a fondness for dissolving in fats, is important in a chemical compound
the reagent is N-trifluoromethylthiosaccharin. saccharin is the cyclic imide of o-sulfobenzoic acid and that imide nitrogen is highly acidic. so saccharin is a good leaving group (cf. the similar compound phthalimide) and so this CF₃S- compound is good for achieving electrophilic trifluoromethylthiolation of a number of substrates (electron-rich aromatics, the alpha position of ketones, etc.)
eh, pretty special purpose, but neat. synthesis is kinda ugly (uses carbon disulfide. ew!)
@Anarkat oh hahaha! well, I suppose there's that touch of forbidden knowledge to this stuff, even though it's all just off a publicly readable website. _Organic Syntheses_ goes back many decades and it's a great resource