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A new approach for the synthesis of some 1,4-benzoxathiin 4,4-dioxide derivatives

✍ Scribed by Ai-Long Fan; Song Cao; Zheng Zhang

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
268 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

A series of 1,4-benzoxathiin 4,4-dioxide derivatives have been prepared by a new synthetic route. The reactions of 2-chloro-4-nitrobenzenethiol 1 with 1 -aryl-2-chloroethanones 2 in the presence of sodium hydroxide give 1-aryl-2-(2-chloro-4-nitrophenylthio)ethanones 3 which on oxidation with (30 %) aqueous hydrogen peroxide afford 1-aryl-2-(2-chloro-4-nitrophenylsulfonyl)ethanones 4 . By the reactions of compounds 4 with 2-[3 or 4-(bromomethyl)phenyl]benzoxazole in the potassium carbonate, triethylbenzylammonium chloride and dimethylformamide system, 2-aryl-3-arylmethyl-7-nitro-1,4-benzoxathiin 4,4dioxides 5 or 6 are obtained via a tandem alkylation-cyclization process.

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Synthesis and carbon-13 nuclear magnetic
Synthesis and carbon-13 nuclear magnetic resonance spectroscopy of 5,6-dihydro-2-methyl-1,4-oxathiin, trans-tetrahydro-1,4-benzoxathiin, 1,4-tetrahydro-[9,10]benzoxathiin, the 4-oxides, 4,4-dioxides and related acyclic compounds
✍ Robert P. Rooney; John C. Dyer; Slayton A. Evans Jr πŸ“‚ Article πŸ“… 1981 πŸ› John Wiley and Sons 🌐 English βš– 674 KB

## Abstract The results of a ^13^C NMR spectral investigation involving 5,6‐dihydro‐1,4‐oxathiins, 1,4‐tetrahydro[9,10]benzoxathiin, __trans__‐tetrahydro‐1,4‐benzoxathiin, and the corresponding sulfoxides and sulfones are reported. An interpretation involving a dipolar structure with (2__p__β†’2__p__