Novel conversion of 6H‐1,3,5‐oxathiazine S‐oxides into 3H‐1,2,4‐dithiazoles by treating with Lawesson's reagent

Abstract

Treatment of 6H-1,3,5-oxathiazine Soxides by Lawesson's reagent (LR) at high temperature furnished 3H-1,2,4-dithiazoles in moderate to good yields. Deoxygenation of 6H-1,3,5-oxathiazine

A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in Organic Syntheses

“…Synthesis of the dithiazole 309 by treatment of oxathiazine S -oxides 308 with P 4 S 10 in refluxing toluene for 1 h was reported, although it was indicated that using LR 566 gave a slightly higher yield (Scheme ) …”

“…Synthesis of the dithiazole 309 by treatment of oxathiazine S-oxides 308 with P 4 S 10 in refluxing toluene for 1 h was reported, although it was indicated that using LR 566 gave a slightly higher yield (Scheme 80). 311 Treatment of P 4 S 10 with chlorine was explained to give a mixture of products, such as sulfur chloride and phosphorus pentachloride (Scheme 81). 312 Application of a similar method, that is addition of chlorine to a mixture of P 4 S 10 and 4-chloroaniline 310 in acetic anhydride at 75 °C, led to the formation of benzothiazathiolium chloride 311, which was reported to be in good yield (Scheme 82).…”

Use of Lawesson's Reagent in Organic Syntheses

“…Conversion of oxathiazine-S-oxides into dithiazoles upon reaction with LR was reported. 430 Reaction of S-oxides 296 with LR in refluxing toluene for 1 h produced the dithiazoles 297, the possible reaction mechanism of which is depicted in Scheme 87.…”