About: Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines

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About: Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The mechanism of sulfurization of substituted triphenylphosphines with 4-(3- and 4-substituted)-1,2,4-dithiazolidine-3,5-diones in acetonitrile, dichloromethane, tetrahydrofuran and toluene at 25 degrees C was studied. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by fast decomposition of the phosphonium intermediate to the corresponding phosphine sulfide, phenylisocyanate and carbonylsulfide. From the Hammett correlations and from the solvent dependency, it was concluded that the transition-state structure is very polar and resembles the zwitter-ionic intermediate. The extent of P-S bond formation and S-S bond cleavage is very similar in the solvents series, but the latter gradually decreases with the decreasing polarity of the solvent. The mechanism of sulfurization of substituted triphenylphosphines with 4-(3- and 4-substituted)-1,2,4-dithiazolidine-3,5-diones in acetonitrile, dichloromethane, tetrahydrofuran and toluene at 25 degrees C was studied. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by fast decomposition of the phosphonium intermediate to the corresponding phosphine sulfide, phenylisocyanate and carbonylsulfide. From the Hammett correlations and from the solvent dependency, it was concluded that the transition-state structure is very polar and resembles the zwitter-ionic intermediate. The extent of P-S bond formation and S-S bond cleavage is very similar in the solvents series, but the latter gradually decreases with the decreasing polarity of the solvent. (en)
Title	Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines (en)
skos:prefLabel	Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines Mechanism of sulfur transfer from 1,2,4-dithiazolidine-3,5-diones to triphenylphosphines (en)
skos:notation	RIV/00216275:25310/13:39896099!RIV14-MSM-25310___
http://linked.open...avai/predkladatel	Fakulta chemicko-technologická
http://linked.open...avai/riv/aktivita	I S
http://linked.open...avai/riv/aktivity	I, S
http://linked.open...iv/cisloPeriodika	7
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Padělková, Zdeňka Hanusek, Jiří Ponomarov, Oleksandr
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Pardubice / Fakulta chemicko-technologická
http://linked.open...dnocenehoVysledku	87025
http://linked.open...ai/riv/idVysledku	RIV/00216275:25310/13:39896099
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	triphenylphosphines; sulfurization; mechanism; kinetics; 5-diones; 4-dithiazolidine-3; 2; 1 (en)
http://linked.open.../riv/klicoveSlovo	4-dithiazolidine-3 5-diones sulfurization triphenylphosphines 1 2 kinetics mechanism
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[342BB66FCCAC]
http://linked.open...i/riv/nazevZdroje	Journal of Physical Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	26
http://linked.open...iv/tvurceVysledku	Padělková, Zdeňka Hanusek, Jiří Ponomarov, Oleksandr
http://linked.open...ain/vavai/riv/wos	000320403000006
issn	0894-3230
number of pages	5 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/poc.3131
http://localhost/t...ganizacniJednotka	25310

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