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Tosylhydrazone information


A tosylhydrazone in organic chemistry is a functional group with the general structure RR'C=N-NH-Ts where Ts is a tosyl group. Organic compounds having this functional group can be accessed by reaction of an aldehyde or ketone with tosylhydrazine.[1]

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595

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Tosylhydrazone

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A tosylhydrazone in organic chemistry is a functional group with the general structure RR'C=N-NH-Ts where Ts is a tosyl group. Organic compounds having...

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Shapiro reaction

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The Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate...

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Spiropentadiene

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bistrimethylsilylpropynone 1 by reaction with p-toluenesulfonylhydrazide to tosylhydrazone 2 followed by treatment with sodium cyanoborohydride to allene 3 and...

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Diazomethane

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Organic Syntheses; Collected Volumes, vol. 8, p. 612. X. Creary (1990). "Tosylhydrazone Salt Pyrolyses: Phenydiazomethanes". Organic Syntheses; Collected Volumes...

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Carbonyl reduction

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Wolff-Kishner reaction. The Caglioti modification, for instance, uses tosylhydrazone with a hydride donor in milder conditions with no base; the Myers modification...

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Alkene

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single ketone can also be converted to the corresponding alkene via its tosylhydrazone, using sodium methoxide (the Bamford–Stevens reaction) or an alkyllithium...

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Hydrazide

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doi:10.1351/goldbook.H02879 Shapiro, Robert H. (1976). "Alkenes from Tosylhydrazones". Org. React. 23 (3): 405–507. doi:10.1002/0471264180.or023.03. ISBN 0471264180...

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Organolithium reagent

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reaction, two equivalents of strong alkyllithium base react with p-tosylhydrazone compounds to produce the vinyllithium, or upon quenching, the olefin...

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Ketene

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the carbonylation of α‐diazocarbonyl compounds and a variety of N‐tosylhydrazones catalysed by Co(II)–porphyrin metalloradicals leading to the formation...

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Diazo

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Diazo compounds are intermediates in the Bamford-Stevens reaction of tosylhydrazones to alkenes, again with a carbene intermediate: In the Doyle-Kirmse...

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