Chloromethylene dimethylammonium

Chloromethylene)dimethylammonium chloride has been used to convert selected alcohols into sulfides in moderate to high yields with inversion of configuration.143... 

Chloromethylene)dimethylammonium chloride171 combines with two molecules of 19 to form the triaminomethane derivative (39).172... 

Chloro-9-(/3-D-ribofuranosyl)purine has similarly been prepared from inosine (63JOC945) by chlorination of 6-thioinosine (63MI40903) or, perhaps most successfully, by reaction of 2, 3, 5 -tri-0-acetylinosine with (chloromethylene)dimethylammonium chloride when yields of 70% are produced (B-78MI40903, p. 611). The latter reagent is obtained from phosgene and DMF in chloroform solution . 

Having assembled the pyrrole core, we endeavored to attach the oxindole side chain and complete the synthesis of 2. Decarboxylation of 12 was achieved in quantitative yield by reaction with H2SO4 in methanol. The a-free pyrrole thus obtained (13) was treated with chloromethylene-dimethylammonium chloride in acetonitrile to form the Vilsmeier adduct 14 in situJ Addition of... 

The versatility of (chloromethylene) dimethylammonium chloride (the Vilsmeier reagent) 27, prepared easily from N,N-dimethylformamide and oxalyl chloride or thionyl chloride, has been observed as an acid activator in the Saudinger reaction. The reaction involving various imines 11 and substituted acetic acids 26 in the presence of this reagent afforded fi-lacams 28 in excellent yields (Scheme 3.11) [35]. 

Chloromethylene dimethylammonium chloride, [MegNCHCll+Cl , can function as a source of co-ordinated carbene, (CHNMej), by three fragment oxidation, salt elimination, or both concurrently. A full paper now details that both the oxidative addition and salt elimination can lead to derivatives for Mo , W , Mn, Re and Co", whereas for V Cr-", Mo ", and... 

C. Reichardt, Vilsmeier-Haack-Arnold Formylations of Aliphatic Substrates with N-Chloromethylene-N,N-dimethylammonium Salts, / Prakt. Chem. 1999, 341, 609-615. 

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