<b>Free Radicals in Amine Solutions of Elemental Sulfur</b>

Hodgson, William G.; Buckler, Sheldon A.; Peters, Grace A.

doi:10.1021/ja00888a012

Cited by 81 publications

(43 citation statements)

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“…By means of ESR measurements Hodgson, Buckler, and felers [49] have found recently that solutions of sulfur in amines contain stable polysulfur radicals ( ; received on April 1 Ith, 19631 a paper describing ESR measurements on the pyrolysis products of diphenyl disulfide and p,p-dinaphthyl disulfide; the products were obtained by methods described by Michaelsen in his thesis. Besides a g value of 2.000, these authors found g = 2.1246 for the pyrolysis product of the disulfide.…”

Section: Aminopolysulfur Radicalsmentioning

confidence: 99%

Free Radicals and Free‐Radical Reactions of Monovalent and Divalent Sulfur

Schmidt¹

1964

Angew. Chem. Int. Ed. Engl.

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Organic free radicals of monovalent sulfur have not been hitherto observed in solution or in melts. Steric hindragce and resonance stabilization, which are responsible ,for the stability of the triarylrnethyl, diphenylnitrogen, and phenoxyl radicals, are apparently insufficient to stabilize the organic free radicals of monovalent sulfur in such concentrations that they can be detected by current physical methods. -I t was only in I963 that arninopolysulfur radicals (R2N-S,, -S.) were detected in solution, and arylsulfur radicals (Ar-S.) and phenylselenium radicals were isolated at ca. -180 "C. -Organically bound sulfur can be stabilized in the free-radical state i f association of the radicals is prevented by fixing in a crystal lattice ("cystine radical"), by repulsion between radical ions (sulfinium salts), or by freezing-in (arylsulfrir radicals).

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Section: Aminopolysulfur Radicalsmentioning

confidence: 99%

Free Radicals and Free‐Radical Reactions of Monovalent and Divalent Sulfur

Schmidt¹

1964

Angew. Chem. Int. Ed. Engl.

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“…Elemental sulfur is readily subjected to S -S bond fission by the reaction with secondary amines (2) strongly assisted by K 2 CO 3 and DMSO as a solvent, to form ammonium salts of thiolate anions 4. 16,17 The reaction of 4 with carbon monoxide gives the carbonylated species 5. Through an elimination of carbonyl sulfide from 5, ammonium salts of thiocarbamates 3 are generated.…”

Section: Resultsmentioning

confidence: 99%

Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur

2004

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“…The present reaction can be proposed in Scheme 1. Salts of thiolates 1 from elemental sulfur and amine react with carbon monoxide to produce carbonyl sulfide (SCO) [13,14]. Deoxygenation of nitroarene with SCO results in the reactive intermediate nitrene 4 [15].…”

Section: Runmentioning

confidence: 99%