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Chemistry of the phenoxathiins and isosterically related heterocycles. XXIII . 1‐azathianthrene: First reported synthesis of a monoazathianthrene and the investigation of the 13 C‐NMR spectrum using two‐dimensional NMR techniques
Author(s) -
PuigTorres Salvador,
Martin Gary E.,
Ford Joseph J.,
Willcott M. Robert,
Smith Keith
Publication year - 1982
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.5570190637
Subject(s) - chemistry , heteronuclear molecule , coupling constant , chemical shift , nuclear magnetic resonance spectroscopy , dimethylformamide , carbon 13 nmr satellite , ring (chemistry) , fourier transform , spin–lattice relaxation , crystallography , fluorine 19 nmr , computational chemistry , stereochemistry , nuclear magnetic resonance , organic chemistry , physics , particle physics , solvent , mathematical analysis , mathematics , nuclear quadrupole resonance
The reaction of the dianion of 3‐mercaptopyridin‐2(1 H )‐thione with 2‐chloronitrobenzene in N,N ‐dimethylformamide leads to the formation of 1‐azathianthrene, the first reported mono‐aza analog of the thianthrene ring system. A partial assignment of the 13 C‐nmr spectrum of the title compound is reported, the assignment based on chemical shift arguments, spin‐lattice (T 1 ) relaxation times and 1 H‐ 13 C spin coupling constants. Amplitude modulated two‐dimensional Fourier transform (AM2DFT) techniques were employed for the acquisition of the heteronuclear spin‐coupling constants.