Chemistry of the Phenoxathiins and Isosterically Related Heterocycles. XXXVII+. The Synthesis and Molecular Structure of Benzo[2,3]Naphtho[5,6,7-ij][1,4]Dithiepin and its 1-Oxide

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Journal Title, Volume, Page: 
Journal of Heterocyclic Chemistry, Volume 26, Issue 3, pages 667–676, May/June 1989
Year of Publication: 
1989
Authors: 
M. J. Musmar
Department of Medicinal Chemistry, College of Pharmacy, University of Houston, Houston, Texas 77204-5515
Current Affiliation: 
Department of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, Nablus, Palestine
Saeed R. Khan
Department of Medicinal Chemistry, College of Pharmacy, University of Houston, Houston, Texas 77204-5515
Andrew S. Zektzer
Department of Medicinal Chemistry, College of Pharmacy, University of Houston, Houston, Texas 77204-5515
Gary E. Martin
Department of Medicinal Chemistry, College of Pharmacy, University of Houston, Houston, Texas 77204-5515
Vincent M. Lynch
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78512
Stanley H. Simonsen
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78512
Keith Smith
Department of Chemistry, University College of Swansea, Singleton Park, Swansea SA2 8PP, U.K.
Preferred Abstract (Original): 

Benzo[2, 3]naphtho[5, 6, 7-ij][1, 4]dithiepin was prepared by the condensation of the disodium salt of 1, 2-dimercaptobenzene with 1-chloro-8-nitronaphthalene. The structure was established by nmr and mass spectroscopy. A small quantity of benzo[2, 3]naphtha[5, 6, 7,ij][1, 4]dithiepin 1-oxide was also isolated. The structure was initially established by mass spectrometry. The proton spectrum was totally assigned using a combination of proton zero quantum coherence (ZQCOSY) and proton-carbon heteronuclear chemical shift correlation (HC-COSY) techniques, which also allowed the unequivocal assignment of the protonated carbon resonances. An X-ray crystal structure of the 1-oxide irrefutably confirmed the structure. The crystal was triclinic and the space group was Pl, and the data refined to a final R = 0.0353. The molecule was shown to be folded about the axis passing through the two sulfur atoms with a dihedral angle of 109.00°.

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Chemistry_of_the_Phenoxathiins_and_Isosterically_Related_Heterocycles._XXXVII+._The_Synthesis_and_Molecular_Structure_of_Benzo[2,3]Naphtho[5,6,7-ij][1,4]Dithiepin_and_its_1-Oxide.pdf2.89 MB