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Preparation of pyrrolo[3,2,1‐ jk ]carbazole by nickel(0) mediated ring contraction of pyrrolo[3,2,1‐ kl ]phenothiazine. Proton NMR and mass spectral studies
Author(s) -
Klingstedt Tomas,
Hallberg Anders,
Dunbar Philip,
Martin Arnold
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220616
Subject(s) - chemistry , phenothiazine , carbazole , proton nmr , mass spectrum , metastability , fragmentation (computing) , carbon 13 nmr , stereochemistry , crystallography , ion , photochemistry , organic chemistry , medicine , computer science , pharmacology , operating system
Pyrrolo[3,2,1‐ jk ]carbazole 1a , the previously unreported 16π‐electron parent compound, has been synthesized by treatment of pyrrolo[3,2,1‐ kl ]phenothiazine 2a with a 1:1 mixture of bis(1,5‐cyclooctadiene) nickel(0) and 2,2′‐bipyridyl. An unequivocal assignment of the 1 H nmr spectrum of 1a was made by decoupling experiments and by comparison with the 1 H nmr spectrum of 1,9‐dideuteriopyrrolo[3,2,1‐ jk ]carbazole 1b . Metastable ion studies, exact mass measurements and the dideuterioderivative 1b were utilized to investigate the electron impact induced fragmentation of 1a .