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Trifluoroacetic acid, Beckmann rearrangement

The Beckmann rearrangement of oximes may be induced by means of dicyclohexylcarbodi-imide and trifluoroacetic acid in dimethylsulphoxide. The oxime (256) of a 17-oxo-steroid gave the usual lactam (257) and seco-nitrile (258). The oxime of a 3a,5a-cyclo-6-ketone gives the ring-B lactam resulting from migration of C(5) (c/. p. 273). A kinetic study of the Beckmann rearrangement... [Pg.281]

Amides lactamsDimethyl thioketals of cyclic or acyclic ketones react with iodine azide to form an a-azido sulfide in 75-95% yield. The product rearranges to an amide or a lactam in high yield in the presence of trifluoroacetic acid. This sequence is an attractive alternative to the Beckmann rearrangement or Schmidt reaction. [Pg.377]

The reaction of 0-(2-acetamido-2-deoxy-D-glucopyranosylidene)-amino-A-phenylcarbamate 53 with trifluoroacetic acid furnished the Beckmann rearranged product 55 and the acid 56. ... [Pg.284]

See other pages where Trifluoroacetic acid, Beckmann rearrangement is mentioned: [Pg.308]    [Pg.410]    [Pg.569]    [Pg.569]    [Pg.569]    [Pg.821]    [Pg.180]    [Pg.56]    [Pg.584]    [Pg.947]    [Pg.821]   
See also in sourсe #XX -- [ Pg.284 ]



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