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[Novel heterocyclic systems. 12.] Chemistry of the phenoxathiins and isosterically related heterocycles. 24. Synthesis of characterization by 13C-NMR spectroscopy of isomeric benzoxathiinopyridazinones: 1-Oxo-1,2-dihydro-2,3-diazaphenoxathiin and 4-Oxo-3,4-dihydro-diazaphenoxathiin. The first observation of a smiles rearrangement involving divalent sulfur during the synthesis of an azaphenoxathiin

Womack, Charles H., Martin, Linda M., Martin, Gary E. and Smith, Keith 1982. [Novel heterocyclic systems. 12.] Chemistry of the phenoxathiins and isosterically related heterocycles. 24. Synthesis of characterization by 13C-NMR spectroscopy of isomeric benzoxathiinopyridazinones: 1-Oxo-1,2-dihydro-2,3-diazaphenoxathiin and 4-Oxo-3,4-dihydro-diazaphenoxathiin. The first observation of a smiles rearrangement involving divalent sulfur during the synthesis of an azaphenoxathiin. Journal of Heterocyclic chemistry 19 (6) , pp. 1447-1452. 10.1002/jhet.5570190638

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Abstract

Condensation of the disodium salt of o-mercaptophenol with 4,5-dichloro-6(1H)-pyridazinone in N,N-dimethylformamide has been observed to lead to the formation of both possible isomeric benzoxathiinopyridazinones. The separation of these isomers, 1-oxo-1,2-dihydro-2,3-diazaphenoxathiin and 4-oxo-3,4-di-hydro-2,3-diazaphenoxathiin and their characterization by 13C-nmr spectroscopy is described. Mechanisms to account for the formation of both isomers are discussed, the most probable mechanism involving a Smiles rearrangement of the phenolate sulfide intermediate formed by the initial displacement of the 4-chloro substituent, providing a specie analogous to a β-halovinylogous ketone.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: This paper represents Part 12 in the series “Novel Heterocyclic Systems.” For the previous paper in this series, see: “Chemistry of the Phenoxathiins and Isosterically Related Heterocycles. XXIII. 1-Azathianthrene: First Reported Synthesis of a Monoazathianthrene and the Investigation of the 13C-NMR Spectrum Using Two-Dimensional NMR Techniques.” S. Puig-Torres, G. E. Martin, J. J. Ford, M. R. Willcott, III, and K. Smith, J. Heterocyclic Chem., 19, 1441 (1982).
Publisher: Wiley
ISSN: 0022-152x
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14524

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