- Use of Piperidine-1-sulphenyl Chloride as a Sulphur-transfer Reagent in Reactions with Diamines: The Preparation of Sulphur-Nitrogen Heterocycles
-
The use of piperidine-1-sulphenyl chloride (3) as a sulphur-transfer reagent in reactions with diamines is described.The reactions of (3) with o-phenylenediamine yielded the dihydro-2,1,3-benzothiadiazole (6) and benzothiadiazole (7).Oxidation of (6) with m-chloroperoxybenzoic acid yielded (7).The reactions of (3) with 1,8-diaminonaphthalene and 1,4,5,8-tetra-aminonaphthalene yielded the 1,2,6-thiadiazine derivatives (14) and (16); possible mechanisms are discussed. 1,2-Diamino-N,N'-dimethylethane and (3) yielded the tetrahydrothiadiazole (17), whereas 1,3-diaminopropane and (3) afforded the novel N-S-N chain compound (19).The reactions of morpholine-1-sulphenyl chloride (4) with aromatic diamines gave the same products in low yields.
- Bryce, Martin R.
-
p. 2591 - 2593
(2007/10/02)
-