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Reactivity of pyrrole pigments, III. Fragmentation of nitro derivatives of pyrrole pigments and its relationship to the Gmelin reaction
Author(s) -
Ribó Josep M.,
Trull Francesc
Publication year - 1983
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198319830102
Subject(s) - chemistry , fragmentation (computing) , pyrrole , pigment , ammonia , bile pigments , nitrous acid , nitro , reactivity (psychology) , yield (engineering) , organic chemistry , medicinal chemistry , ecology , medicine , alkyl , alternative medicine , materials science , pathology , metallurgy , biology
The 5‐(arylnitromethylene)‐3‐pyrrolin‐2‐ones 1‐5 , the 5‐nitrobilin‐ 1,19 ‐diones 7,8 , and the 5‐nitropyrromethenone 6 are shown to decompose in acidic media to yield maleimides according to fragmentation reactions of nitronic acids. This fragmentation reaction elucidates the nature of the Gmelin reaction and the formation of the “Nitritkörper” (methylvinylmaleimide) by nitrous acid treatment of bilirubin.