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 ORCID: https://orcid.org/0000-0003-4838-5651 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:	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:	https://orca.cardiff.ac.uk/id/eprint/12644

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