The Formation of 4-Chlorodibutylamine from N-Chlorodibutylamine<sup>1</sup>

Wawzonek, S.; Culbertson, Townley P.

doi:10.1021/ja01522a053

Cited by 33 publications

(17 citation statements)

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“…Bchwefelsaure mit Eisen-11-salz die Radikslkettenreaktion auslosten. Fiir den intramolekularen Radikalangriff war zwar damit zu rechnen, daB spezifisch &Positionen angegriffen wiirden [9], so daB keine anderen RinggroBen als Fiinfringe auftreten wiirden ; es war aber mit gleicher Wahrscheinlichkeit mit der Bildung des gewunschten Produktes 1 und eines Isomeren 6 zu rechnen, da zwei gleichwertige &Positionen zur Verfugung standen. TatsLchlich zeigte das Massenspektrum des auf sekundiire Amine aufgearbeiteten Reaktionsproduktes, daB ein Molpeak der fur 1 bzw.…”

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Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

1980

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Syntheses of trail Pheromones of the Pharao Ant (Monomorium pharaonis (L.)) Hofmann‐Löffler‐reaction, starting from 5‐amino‐tridecane yields pyrrolidine mixtures containing 2‐butyl‐5‐pentyl‐pyrrolidine 1, known as a trail pheromone of the Pharao ant. An analogous reaction of 7‐amino‐pentadecane leads to 2‐hexyl‐5‐pentyl‐pyrrolidine 2 as a mixture with an isomer. Definite 2,5‐dialkyl‐pyrrolidines are obtained by Seebach alkylation from N‐nitroso‐pyrrolidines e.g. 1, 2 or 3, the latter with an unsaturated side chain. Change of reaction conditions led to 2,2‐dialkyl‐pyrrolidines. Dehydrogenation followed by hydrogenation converts a mixture of cis‐trans‐isomers of 1 into definite cis‐compound 1a. Trails of these pyrrolidines are followed by Pharao ants.

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Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

1980

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“…Intramolecular aliphatic C–H amination is a vital transformation to synthesize diverse biologically active heterocyclic scaffolds with C–N bonds. The Hofmann‐Loffler‐Freytag (HLF) reaction is a valuable method implemented by Suarez and Co‐workers for the formation non‐activated C(sp 3 )‐N bonds by using the mixture of iodobenzene diacetate (PIDA, 1 ) and molecular I 2 to generate the key nitrogen radical intermediate.…”

Section: Intramolecular Oxidative C(sp3)‐n Bond Formationmentioning

confidence: 99%

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

et al. 2019

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Hypervalent iodine chemistry is a rapidly growing area of research with tremendous impact on synthetic chemistry in the past years. A rich and diverse chemistry is now available for reactions using hypervalent iodine reagents, as metal‐free, ecofriendly reagents and the advent of new reactions will be of large benefit to researchers working in the area of selective synthesis. In this review article, we emphasize the usage of hypervalent iodine(III) reagents for metal‐free intramolecular oxidative C–N bond formation/annulation to synthesize wide range of N‐heterocycles in organic synthesis. The functionalization of C–H bonds through the involvement of sp‐, sp2‐, and sp3‐hybridized carbon atoms for cyclizations is discussed in detail.

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“…from the starting material by a reactive intermediate, IIIa or VII, respectively. Starting with a cyclic amine, a prediction of the intermediate products is shown in [4]. The parent compounds IX would lose an electron on the anode to give a cation radical X.…”

Section: Introductionmentioning

confidence: 99%

“…Since protonation is prevented in basic media, bicyclization would be encouraged. Reaction [4] shows the loss of two electrons and two protons in routes A and B.…”

Section: Introductionmentioning

confidence: 99%

Bicyclization of aza-compounds by positive halide ions. I. Cyclic amines

Elofson¹,

Gadallah²,

Laidler³

1985

Can. J. Chem.

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Cyclic amines are oxidized to the bicyclic compounds by electrochemical oxidation. The presence of halide ions is found necessary for the reaction to proceed and to produce any bicyclic products. It is postulated that a positive halide species, X(+), is produced electrochemically and stabilized under the specific reaction conditions. The X(+) ion forms a complex with the parent cyclic amine which decomposes to the bicyclic product and HX. An analogy between the Hofer–Moest reaction to produce C(+) and this reaction to produce X(+) is postulated

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The Formation of 4-Chlorodibutylamine from N-Chlorodibutylamine¹

Cited by 33 publications

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Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

Bicyclization of aza-compounds by positive halide ions. I. Cyclic amines

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The Formation of 4-Chlorodibutylamine from N-Chlorodibutylamine1

Cited by 33 publications

References 0 publications

Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

Synthesen von trail‐Pheromonen der Pharaoameise (Monomorium pharaonis(L.))

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

Bicyclization of aza-compounds by positive halide ions. I. Cyclic amines

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The Formation of 4-Chlorodibutylamine from N-Chlorodibutylamine¹