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Pseudohalogens reactions with alkenes

Bis [(trifluoromethyl)thio] acetaldehyde (83a) has been prepared from an enam-ine precursor (84), although refluxing in aqueous ethanolic HCl is required to effect this reaction.The aldehyde is less stable than its enol tautomer (83b), and many reactions typical of aldehydes fail. For example, addition of aqueous silver nitrate immediately yields the silver salt of (83b), rather than giving precipitation of (elemental) silver. The (trifluoromethyl)thio substituent has pseudohalogenic character and, together with the hydroxy group, stabilizes the alkene tautomer in the manner of a push-pull alkene. The enol-aldehyde equilibrium mixture in acetonitrile shows an apparent of 2.6 when titrated with aqueous hydroxide. [Pg.24]

See other pages where Pseudohalogens reactions with alkenes is mentioned: [Pg.47]    [Pg.440]    [Pg.83]    [Pg.83]    [Pg.83]    [Pg.440]    [Pg.682]    [Pg.136]    [Pg.83]    [Pg.305]   
See also in sourсe #XX -- [ Pg.4 , Pg.348 , Pg.349 , Pg.350 , Pg.351 , Pg.352 , Pg.353 , Pg.354 , Pg.355 ]

See also in sourсe #XX -- [ Pg.4 , Pg.348 , Pg.349 , Pg.350 , Pg.351 , Pg.352 , Pg.353 , Pg.354 , Pg.355 ]



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Pseudohalogen

Pseudohalogens

Pseudohalogens reactions with

Reaction with alkenes

Reactions pseudohalogens

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