Picrylpyridinium chloride

The acid chloride of i i7-nitromethane, CH2=N(C1)0 (mp —43°C, bp 2—3°C), is formed by fusion of nitromethane and picrylpyridinium chloride (36). It is hydroly2ed to nitro some thane, reduces potassium permanganate strongly, and exhibits no reactions characteristic of hydroxamic acids. 

Picryl chloride (87) reacts with pyridine to form picrylpyridinium chloride (93), a useful intermediate which reacts with a range of nucleophiles 2,4,6-trinitrodiphenylamine and 2,4,6-trinitrodiphenylether can be formed from aniline and phenol respectively. 2,4,6-Trinitrodiphenylamine is readily nitrated with mixed acid to the high explosive 2,2, 4,4, 6,6 -hexanitrodiphenylamine (hexyl). 

Picryl chloride reacts with pyridine to form picrylpyridinium chloride (IV)... 

Okon [34] in a number of investigations found that when picrylpyridinium chloride reacts with phenols or aromatic amines, derivatives of trinitrodiphenyl oxide or trinitrodiphenylamine are obtained ... 

On treating picrylpyridinium chloride with alcohol Hodges [35] obtained picryl-... 

By melting a mixture of 2-pyridone and picrylpyridinium chloride, the O- and A -alkylated products (W-508and W-509) are formed in 17%and 82%yield, respectively. Rearrangement of XII-S08 to XII-S09 occurs at its melting point. The silver salt of 2-pyridone and picryl chloride in benzene gives 97%of XII-S08 and 3%of Xn-509. ... 

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