1,5-Dithia-2,4,6,8-tetrazocine: A Novel Heterocycle of Unusual Properties

I. Ernest*, W. Holick, G. Rihs, D. Schomburg, G. Shoham, D. Wenkert, R. B. Woodwardt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

94 Scopus citations

Abstract

Four representatives of a novel heterocycle-l,5-dithia-2,4,6,8-tetrazocine-were prepared. In the 3,7-diphenyl (3) and 3,7-bis(p-methoxyphenyl) (5) derivatives, the eight-membered ring was found to be planar by X-ray diffraction analysis; this and the bond lengths as well as the electronic spectra suggest a delocalized, aromatic system of 10 π electrons. On the other hand, 3,7-bis(dimethylamino)-1,5-dithia-2,4,6,8-tetrazocine (4) is folded along an axis drawn through the sulfur atoms; the short distance between the latter atoms is suggestive of their partial bonding in this compound.

Original languageAmerican English
Pages (from-to)1540-1544
Number of pages5
JournalJournal of the American Chemical Society
Volume103
Issue number6
DOIs
StatePublished - Mar 1981
Externally publishedYes

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