75184-37-1Relevant academic research and scientific papers
On the reaction of 1,3-dichloro-2-azoniaallene salts with isocyanates and carbodiimides
Ismail,Hamed,Hitzler,Troll,Jochims
, p. 820 - 826 (1995)
1,3-Dichloro-2-azoniaallene salts 1 react with one or two equivalents of isocyanates 2 to afford nitrilium salts 4, together with allophanoyl chlorides 5 or carbamoyl chlorides 8. The chlorides 5 and 8 were characterized by their reactions with nitrogen nucleophiles (products 10-12, 14). With antimony pentachloride, the allophanoyl chlorides 5 cyclize to 2-chloro-substituted 1,3,5-oxadiazinium salts 13. The chloro-substituted 2-azoniaallene salt 15 was obtained from the reaction of 8f with a ketone in the presence of antimony pentachloride. The 1,3-diaryl-1,3-dichloro-2-azoniaallene salt 1f adds to carbodiimides 16 to form labile 2,2-dichloro-1,3,5-triazinium salts 17, which were characterized as derivatives 18-20.
On the synthesis of nitrilium salts from nitriles and chloroformates
Shrestha-Dawadi,Jochims
, p. 426 - 432 (2007/10/02)
Nitriles react with methyl or ethyl chloroformate (2a,b) and antimony(V) chloride to give high yields of N-methyl-, or N-ethylnitrilium hexachloroantimonates 3,4. With butyl chloroformate (2c) N-(1-methylpropyl)nitrilium salts 6 are obtained. These products arise from a 2-butyl cation, which is formed prior to alkylation of the nitrile. Isobutyl chloroformate (2d), (2-tert-butylcyclohexyl) chloroformate (2e), menthyl chloroformate (2f), 2,2-dimethylpropyl chloroformate (2g), and 3-methylbutyl chloroformate (2h) react with nitriles to give N-tert-alkylnitrilium salts, 11,13,15,19, which were characterized by hydrolysis to amides. With phenyl chloroformate (2i) benzonitriles react in a 1:2 ratio to furnish 2-phenoxy-1,3,5-oxadiazinium salts 21.
