1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(III) compounds - a kinetic comparative study

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F12%3A39894707" target="_blank" >RIV/00216275:25310/12:39894707 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1039/c2ob26460a" target="_blank" >http://dx.doi.org/10.1039/c2ob26460a</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c2ob26460a" target="_blank" >10.1039/c2ob26460a</a>

Result language

angličtina

Original language name

1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(III) compounds - a kinetic comparative study

Original language description

The sulfurization efficiency of 25 3-substituted-1,2,4-dithiazole-5-ones and 5-thiones towards triphenyl phosphite in acetonitrile, DCM, THF and toluene at 25 degrees C was evaluated. All the 1,2,4-dithiazoles are much better sulfurizing reagents than commercially available agents (PADS, TETD, Beaucage's reagent). The most efficient sulfurizing agents in all solvents are 3-phenoxy (4), 3-phenylthio (5) and 3-ethoxy-1,2,4-dithiazole-5-one (1) whose reactivity is at least two orders of magnitude higher than that of other 1,2,4-dithiazoles. Contrary to a previous report, the sulfurization with 1 does not yield carbonylsulfide and ethyl cyanate as the additional reaction products but unstable ethoxythiocarbonyl isocyanate which has been trapped with 4-methoxyaniline. Similar trapping experiments have proven that the site of attack is at the sulfur adjacent to the C = O group for compounds 4 and 5. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2012

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

10

Issue of the periodical within the volume

44

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

8868-8876

UT code for WoS article

000310216300017

EID of the result in the Scopus database

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