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Chemistry of the phenoxathiins and isosterically related heterocycles. 37. The synthesis and molecular structure of benzo[2, 3]naphtho[5, 6, 7-ij][1, 4]dithiepin and its 1-oxide

Musmar, M. J., Khan, Saeed R., Zektzer, Andrew S., Martin, Gary E., Lynch, Vincent M., Simonsen, Stanley H. and Smith, Keith 1989. Chemistry of the phenoxathiins and isosterically related heterocycles. 37. The synthesis and molecular structure of benzo[2, 3]naphtho[5, 6, 7-ij][1, 4]dithiepin and its 1-oxide. Journal of Heterocyclic chemistry 26 (3) , pp. 667-676. 10.1002/jhet.5570260328

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Abstract

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°.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: This paper also represents Part 33 in the Series Novel Heterocyclic Compounds. For the preceeding paper in that series, see: K. Smith, C. M. Lindsay and I. K. Morris, “Convenient Syntheses of 4-Aminopyridine-3-thiol and Several Thiazolo[5, 4-c]pyridines”, in preparation. For the previous paper in the series Chemistry of the Phenoxathiins, see: The paper cited in ref[11] of this work.
Publisher: Wiley
ISSN: 0022-152x
Last Modified: 04 Jun 2017 02:50
URI: http://orca.cf.ac.uk/id/eprint/12644

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