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Upstream product

• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 193743-67-8 2-(2-Oxo-2-phenyl-ethanesulfinyl)-isoindole-1,3-dione 
• 98-86-2 acetophenone 
• 85260-02-2 2-(2-Oxo-2-phenyl-ethylsulfanyl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

Novel Type Elimination Reactions of Sulfoxides Bearing Several Heteroaromatics: Trapping of Sulfines with 2,3-Dimethyl-1,3-butadiene

Previously we reported the novel thioaldehydes generation via thermolyses of phenacyl sulfoxides bearing some heteroaromatics. Thermolysis of sulfoxides (1a,b and 2a-4a) bearing other heterocycles such as thiadiazole, triazole, and tetrazole in the presence of 2,3-dimethyl-1,3-butadiene in dioxane at 100 °C led to the unexpected products 6-substituted-5,6-dihydro-3,4-dimethyl-2H-thiapyran 1-oxide (5a,b). These products were considered to be formed by the Diels-Alder reaction of the diene with the sulfines formed initially by the thermal decomposition of the sulfoxides. The rate acceleration and the improvement of the yield by addition of 1.5 equiv of triethylamine, especially in the case of ethoxycabonylmethyl sulfoxide 1c, was observed. The cis-trans selectivity for sulfine cycloadducts was also studied by NMR spectrometry. The reactions of α-substituted phenacyl sulfoxides 1d-f bearing a phenyl-substituted tetrazolyl group in the presence of the same diene were also studied.

α-Oxosulfines part 3. Generation and trapping of α-Oxothioaldehyde S- oxides

α-Oxothioaldehyde S-oxides 4a-f can be generated under very mild conditions from the corresponding sulfinyl compounds 3a-f, which in turn are obtained by m-chloroperoxybenzoic acid (MCPBA) oxidation of α- oxothiophthalimides 2a-f. The reactive sulfine intermediates can be trapped as electron-poor dienophiles as well as electron-poor dienes with formation of dihydrothiopyran S-oxides 5a-e or 1,4-oxathiin S-oxides 6a-f, respectively.