Trichloroacetonitrile, 98%, Thermo Scientific Chemicals

General References:

1. The combination with PPh₃ is superior to the popular CCl₄-PPh₃ system for conversion of carboxylic acids to acyl chlorides: Tetrahedron Lett., 40, 5323 (1999). It also converts allylic alcohols to the corresponding chlorides: Russ. J. Org. Chem., 31, 1019 (1995).
2. In the presence of a base, e.g DBU, reacts with alcohols to form trichloroacetimidates, which are a useful means of protection, readily cleaved by TsOH/MeOH, DBU/MeOH or ZnH₄Cl: Synlett, 753(1999). These imidates are activated towards displacement by nucleophiles. Glycosyl imidates, formed in the presence of a base such as K₂CO₃ or DBU, are widely applied as glycosyl donors in oligosaccharide synthesis. Reaction with the free OH of the glycosyl acceptor occurs under mild conditions, promoted by a Lewis acid, e.g. BF₃ etherate or TMS-OTf, to form, respectively, either the ß- or ɑ-glycoside as the major product: Angew. Chem. Int. Ed., 25, 212 (1986). For reviews, see: Chem. Rev., 93, 1503 (1993); Adv. Carbohydr. Chem. Biochem., 50, 21 (1994); Contemp. Org. Synth., 3, 173 (1996). The imidates of allylic alcohols, prepared using NaH, or, more conveniently, KOH under phase-transfer conditions: Tetrahedron Lett., 37, 1481 (1996), undergo a [3,3]-sigmatropic rearrangement to derivatives of allylamines: J. Am. Chem. Soc., 96, 597 (1974); 98, 2901 (1976). For an example, see: Org. Synth. Coll., 6, 507 (1988). Review: Acc. Chem. Res., 13, 218 (1980):
3. Aromatic aldoximes are dehydrated to nitriles by a similar cyclic mechanism: J. Org. Chem., 38, 2241 (1973).
4. Reacts with hydrogen peroxide, to give, in situ, peroxytrichloroacetamidic acid, a reagent for the epoxidation of alkenes under essentially neutral conditions: J. Org. Chem., 48, 888 (1983).
5. For a review of the chemistry of trichloroacetonitrile, see: Heterocycles, 43, 1083 (1996).