THE CHAIN LENGTHENING OF ALIPHATIC ALDEHYDES WITH THE AID OF "NUCLEOPHILIC CARBENE"

Article abstract of DOI:10.1016/S0040-4039(00)93683-9

The addition of "nucleophilic carbene" on 1,2,4-triazole bases (2) and aldehydes is decisively influenced by the anion present. 5-(α-Hydroxyalkyl)-1,2,4-triazolium chlorides, formed in the addition reaction of 3-methylthio-1,4-diphenyl-1,2,4-triazolium chloride (1c) with aldehydes, can be easily reduced to 5-alkyl-1,2,4-triazolium iodides (5).Reduction of these with NaBH4 affords aldehydes by acidic hydrolysis or carboxylic acids by alkaline hydrolysis, the carbon chain of which has been lengthened by one CH2 group, as compared to the starting aldehyde.