Formylations oxalyl chloride-dimethylformamide

Formylation. Vilsmeier formylation reactions have been reviewed. Oxalyl chloride-dimethylformamide has found occasional use one application has been preparation of a piperidine substituted dialdehyde (eq 10). ... 

The main applications of oxalyl chloride, as described in Chapter 4, are the formation of aryl isocyanates and chloroformates (by reactions with amines and hydroxylic substrates, respectively), and the formation of acyl chlorides from carboxylic acids under very mild conditions. Oxalyl chloride reacts with amides to give acyl isocyanates, and it is used with dimethyl sulfoxide as a mild reagent for the oxidation of alcohols (Swern-type oxidation). It is also used with N,N-dimethylformamide as a mild reagent for chlorination and formylation. Oxalyl chloride is widely used in commercial formulations of speciality polymers, antioxidants, photographic chemicals, X-ray contrasting agents, and chemiluminescent materials. Other physical properties are presented in Chapter 3. 

N-Vinylpyrroles were also formylated by dimethylformamide-oxalyl chloride (CH2CI2, rt, 40 min) to give the corresponding N-vinylpyrrole-2-carbaldehydes 157 in yields up to 97% (09S587). 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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