Ueber Cyclooctene

Willstätter, Richard; Hans, Veraguth,

doi:10.1002/cber.190503802128

Cited by 27 publications

(6 citation statements)

References 11 publications

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“…Formanilides were reduced to the corresponding N- methylanilines by the method similar to that of Brown and Heim N- methyl-4-chloroaniline, N,N ‘-diformyl- p -phenylenediamine, N- nitroso- N- methyl-4-chloroaniline ( 2 X = Cl), N,N ‘-dinitroso- N,N ‘-dimethyl- p -phenylenediamine ( 13 ), N,N- dimethyl-4-chloroaniline (prepared by a modification of the method of Borsch and Hassid), N,N,N ‘, N ‘-tetramethyl-2-nitro- p -phenylenediamine ( 3 , X = N(CH 3 ) 2 ), and 4-chloro-2-nitrodimethylaniline ( 3 , X = Cl).…”

Section: Methodsmentioning

confidence: 99%

Evidence for Radical Cations in Linked Mechanisms of N,N-Dialkyl Aromatic Amine Nitration and Nitrosative Dealkylation

et al. 1998

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N,N-Dialkyl aromatic amines react rapidly with nitrous acid to competitively produce a nitrosamine and a nitro compound. The mechanism of nitro compound formation involves a reaction of an amine radical cation with NO2, while the nitrosamine is produced by two competing pathways, one of which involves N-α-CH deprotonation of a radical cation with subsequent oxidative generation of an imminium ion, and the other of which occurs through NOH elimination of a nitrosammonium ion (R3N−NO+). All three pathways are linked through the reversible homolysis of R3N−NO+ to NO and a radical cation.

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Section: Methodsmentioning

confidence: 99%

Evidence for Radical Cations in Linked Mechanisms of N,N-Dialkyl Aromatic Amine Nitration and Nitrosative Dealkylation

et al. 1998

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“…A few of the experimental observations of electrolytic reduction, however, are explicable most easily upon the free radical hypothesis. By the electrolytic reduction of ketones, pinacones are produced, whilst aldehydes can yield glycols (166,148,136). Pinacone (pinacol) formation can be explained most simply as due to combination of two free ketyl radicals: In the same way sodium benzophenone, (CeH^CONa, yields benzopinacol, (C6H6)2COH…”

Section: A Cathode Reactionsmentioning

confidence: 99%

Some Organic Reactions Involving the Occurence of Free Radicals in Solution.

Hey¹,

Waters²

1937

Chem. Rev.

110

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“…C. CYCLOOCTADIENES 1,5-Cycloóctadienes are prepared by dimerization of 1,3-butadienes (see pages [110][111], by degradation of N, V-dimethyl-4-cycloocten-l-ylamine (161,163,173,174), and by dehydrobromination of 5-bromocyclooctene (174).…”

Section: B Cyclooctatrienesmentioning

confidence: 99%

“…Willstátter and Veraguth (161,163) reported that pyrolysis of the quaternary hydroxide of N, N-dimethyl-4-cycloócten-l-ylamine gives a very unstable CgHu hydrocarbon, and that addition of two molar equivalents of hydrogen bromide to this unstable C8Hi2, followed by treatment with alkali or quinoline, gives a stable C8Hi2 hydrocarbon. The unstable hydrocarbon was designated a-cyclooctadiene and the stable, /3-cyclooctadiene.…”

Section: B Cyclooctatrienesmentioning

confidence: 99%

“…1,5-Cyclooctadiene forms a crystalline silver nitrate addition product (37) and is readily hydrogenated to cyclooctane (24,160,163,173,174). It adds stepwise one or two molar equivalents of bromine (161,174) or hydrogen bromide (163,174). The mono hydrogen bromide addition product, 5-bromocyclooctene (II), is converted to the carboxylic acid (III) by carbonation of the Grignard reagent or to N, V-dimethyl-4-cycloocten-1 -ylamine (IV), along with some 1,5-and 1,4-cyclooctadiene, by treatment with dimethylamine (174).…”

mentioning

confidence: 99%

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