caa a22 4500 475759303 CHVBK 20180406123546.0 cr unu---uuuuu 170329e20000901xx s 000 0 eng 10.1007/BF02495148 doi (NATIONALLICENCE)springer-10.1007/BF02495148 Kinetics, products, and mechanism of the reaction of diphenylcarbonyl oxide with sulfoxides [Elektronische Daten] [A. Nazarov, E. Chainikova, P. Krupin, S. Khursan, I. Kalinichenko, V. Komissarov] The kinetics of the reactions of diphenylcarbonyl oxide with dimethyl, di-n-hexyl, diphenyl, dibenzyl, andn-hexylbenzyl sulfoxides in acetonitrile was studied by flash photolysis at 295 K. The oxidation of sulfoxide affords the corresponding sulfone as the main reaction product, and diphenyl sulfide also forms in the case of Ph2SO. Solvent effect on the reaction kinetics and the composition of the reaction products was studied. The reaction mechanism is discussed, which includes two parallel pathways: the nucleophilic attack of carbonyl oxide at the sulfur atom of sulfoxide and the formation of the cyclic sulfurane intermediatevia the electrophilic 1,3-cycloaddition of Ph2COO at the S=O bond. The sulfurane undergoes fragmentationvia parallel channels to form sulfone or sulfide. Kluwer Academic/Plenum Publishers, 2000 kinetics nationallicence flash photolysis nationallicence carbonyl oxides nationallicence sulfoxides nationallicence Nazarov A. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut Chainikova E. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut Krupin P. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut Khursan S. Bashkortostan State University, 32 ul. Frunze, 450074, Ufa, Russian Federation aut Kalinichenko I. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut Komissarov V. Bashkortostan State University, 32 ul. Frunze, 450074, Ufa, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/9(2000-09-01), 1496-1500 1066-5285 49:9<1496 2000 49 11172 https://doi.org/10.1007/BF02495148 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495148 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Nazarov A. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut NATIONALLICENCE 700 1- Chainikova E. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut NATIONALLICENCE 700 1- Krupin P. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut NATIONALLICENCE 700 1- Khursan S. Bashkortostan State University, 32 ul. Frunze, 450074, Ufa, Russian Federation aut NATIONALLICENCE 700 1- Kalinichenko I. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation aut NATIONALLICENCE 700 1- Komissarov V. Bashkortostan State University, 32 ul. Frunze, 450074, Ufa, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/9(2000-09-01), 1496-1500 1066-5285 49:9<1496 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer