(2E,6E)‐2,6‐Bis(organylchalogenylmethylidene) substituted 1,4‐dithiane 1,1,4,4‐tetraoxides and N‐organyl thiomorpholine 1‐oxides as new S‐oxide derivatives of bis(2‐organylchalcogenylvinyl) sulfides

• Published in: Heteroatom chemistry Vol. 29; no. 2
• Main Authors: Martynov, Alexander V., Makhaeva, Nataliya A., Amosova, Svetlana V.
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.03.2018; Hindawi Limited
• Subjects: (2E,6E)‐2,6‐bis(chloromethylidene)‐1,4‐dithiane 1,1,4,4‐tetraoxide; (2E,6E)‐2,6‐bis(chloromethylidene)‐N‐organyl thiomorpholine 1‐oxides; Chemistry; Chemistry, Multidisciplinary; Mass spectrometry; NMR; NMR spectroscopy; Nuclear magnetic resonance; Nucleophiles; nucleophilic vinylic substitution; organyl chalcogenolate; Oxides; Physical Sciences; Science & Technology; Substitution reactions; 4-dithiane 1; OXIDATION; METHANOL; 6-bis(chloromethylidene)-N-organyl thiomorpholine 1-oxides; 6E)-2; nucleophilic vinylic substitution; DISULFIDES; REDUCTIONS; 1; 4-tetraoxide; SODIUM-BOROHYDRIDE; CHALCOGENIDES; 2E; 4; organyl chalcogenolate; NMR spectroscopy; (2E,E)-2,6-bis(chloromethylidene)-1
• ISSN: 1042-7163; 1098-1071
• DOI: 10.1002/hc.21420

It is shown that (2E,6E)‐2,6‐bis(chloromethylidene)‐N‐organyl thiomorpholine 1‐oxides and (2E,6E)‐2,6‐bis(chloromethylidene)‐1,4‐dithiane 1,1,4,4‐tetraoxides, unlike unoxidized analogs, (2E,6E)‐2,6‐bis(chloromethylidene)‐N‐organyl thiomorpholines, and (2E,6E)‐2,6‐bis(chloromethylidene)‐1,4‐dithiane, easily undergo stereoselective nucleophilic vinylic substitution reactions with such chalcogen‐containing nucleophiles as sodium 1‐butanethiolate, arenethiolates, and benzeneselenolate to afford previously unknown (2E,6E)‐2,6‐bis(organylchalogenylmethylidene)‐N‐organyl thiomorpholine 1‐oxides and (2E,6E)‐2,6‐bis(organylchalogenylmethylidene)‐1,4‐dithiane 1,1,4,4‐tetraoxides in high yields. The structures of the heterocycles formed have been confirmed by 1H, 13C NMR, and mass spectrometry data.