CXIX.—The interaction of hydrogen sulphide, thiocyanogen, and thiocyanic acid with unsaturated compounds

Challenger, Frederick; Smith, Alan; Paton, Frederic James

doi:10.1039/ct9232301046

Cited by 16 publications

(2 citation statements)

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“…Br À . The Ph 3 P/(SCN) 2 system gives Ph 3 P=S immediately 40 ; the Ph 3 P/PhSSPh system in methanol giving Ph 3 P=0, PhSH and PhSMe, 41 was not tested for its reduction ability. Protonated by 20 mol% p-toluenesulphonic acid, allylarsonic acid in methanol consumes the Ph 3 P in ca 6 h at RT.…”

Section: Iodide-catalysed Reductionsmentioning

confidence: 99%

On the direct reduction of arsonic acids to arsenoso compounds: mechanisms and preparations

Ioannou

2000

Appl. Organometal. Chem.

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By using a variety of reducing agents, either alone or in the presence of iodide as a catalyst, the reduction of arsonic acids to arsenoso compounds and/or arsonous acids has been studied. The solvent and temperature are important for a clean reduction. The mechanism of the reduction involves prior protonation of the AsO3H2 group, and can be rationalized in the framework of the ‘hard and soft acids and bases’ principle, which is used to predict other reducing systems and to explain other literature data. For preparative purposes, triphenylphosphine/iodine, hexamethylphosphorous triamide/iodine and ascorbic acid/iodine give flexibility of choice depending on the substrate. The first two of these systems decompose arsonic acids with a weak C–As bond but the last system is sufficiently mild towards the same arsonic acids. Copyright © 2000 John Wiley & Sons, Ltd.

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Section: Iodide-catalysed Reductionsmentioning

confidence: 99%

On the direct reduction of arsonic acids to arsenoso compounds: mechanisms and preparations

Ioannou

2000

Appl. Organometal. Chem.

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“…Vibrational frequencies due to skeleton vibrations for both the trialkyl and triarytantimony(V) pseudohalides, RaSbX2 [R = alkyl or phenyl; X = N3 lss'lg°'191q93), NCO188,193) NC5188, [194][195][196]] and (Ph3SbX)20 [X = N3, NCO, NCS] Iss), have generally been interpreted in terms of a D3h skeleton symmetry. A trigonal bipyramidal geometry having pseudohalide moieties at the axial positions has been suggested.…”

Section: Pseudohalides Oxides and Related Compoundsmentioning

confidence: 99%

Structure and bonding in organic derivatives of antimony(V)

Jain

Bohra

Mehrotra

1982

Structures Versus Special Properties

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Substitution and Addition Reactions of Thiocyanogen*Present address, School of Biological Sciences, The Medical School, University of Tennessee, Memphis, Tenn.

Wood

2011

Organic Reactions

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The direct replacement of a hydrogen atom by a thiocyano group through the use of thiocyanogen is termed thiocyanation. This replacement reaction is limited practically to aromatic amines and phenols. Thiocyanogen reacts with olefinic and acetylenic linkage, the reagent adding to the unsaturated linkage. Thicyanogen reacts with compounds of other types. Thiocyanogen reacts with aromatic compounds that are highly susceptible to substitution with the introduction of a thiocyano groups. Thiocyanation of aromatic amines, phenols is discussed. Addition of thiocyanogen to olefins and acetylenes, and miscellaneous syntheses are also discussed.

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CXIX.—The interaction of hydrogen sulphide, thiocyanogen, and thiocyanic acid with unsaturated compounds

Cited by 16 publications

References 0 publications

On the direct reduction of arsonic acids to arsenoso compounds: mechanisms and preparations

On the direct reduction of arsonic acids to arsenoso compounds: mechanisms and preparations

Structure and bonding in organic derivatives of antimony(V)

Substitution and Addition Reactions of Thiocyanogen*Present address, School of Biological Sciences, The Medical School, University of Tennessee, Memphis, Tenn.

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