79482-92-1Relevant academic research and scientific papers
Reactions with Isocyanides. - Synthesis of Dark-blue Dyes from 1,4-Quinones and Aryl Isocyanides
Ott, Walter,Formacek, Viktor,Seidenspinner, Hubert-Matthias
, p. 1003 - 1012 (2007/10/02)
1,4-Benzoquinone reacts with aryl isocyanides 2a - d in boiling toluene or xylene forming dark-blue 1:2 and 1:4 adducts, the 4,7-isoindolediones 3a - d and the 1,5- and 1,7-bis(arylamino)benzodipyrrolediones 4a - c and 5a - c, respectively, which can be separated by chromatography.The structure of the 4-methylphenyl isocyanide adducts 3b, 4b, and 5b is established by NMR spectroscopy.The 1:2 adduct 3b reacts with two moles of 4-methylphenyl isocyanide (2b) affording the isomeric 1:4 adducts 4b and 5b.However, in a similar reaction with 4-chloro-phenyl isocyanide (2c) surprisingly only the 1,5-bis(arylamino) derivative 8 is isolated. 1,4-Naphthoquinone (10) reacts with 4-methylphenyl (2b) or 4-nitrophenyl isocyanide (2d) to yield the 4,9-benzoisoindoles 11b and d, respectively.
