Imidium salts

Substituted thiolactams (65) are obtained from lactams (63) in SS-100% yield by alkylation with Meerwein reagent and subsequent thiolysis of the resulting imidium salt (64 equation 29). The ap-proach has been extended to other thiolactams and acyclic examples employing a cyanohydrin derivative (66 equation 30). Similarly, A, N-acetals of formyl cyanide, (R2N)2CHC N, yield thioformamides on treatment with HaS. ... 

In an extension of this triazine synthesis, dithiocarbamates 8, rather than amides, can be employed. In this case the corresponding imidium salts are obtained by reaction of the dithiocarbamates with phosgene or chlorine.395 396... 

N,N-dihalogenamines 26, 269 Immoninm salts (s. a. Imidium salts) s. azomethinium salts cyclimmonium -Indan-l,3-diones (s. a. Ninhydrin)... 

Thionyl chloride, phosphonis(V) chloride, and triphenylphosphine/tetrachloro-methane can be used to convert monosubstituted amides into chloro imines. These reagents, as well as oxalyl chloride, also transform disubstituted amides into the corresponding imidium chloride salts. 

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