382. The diazotisation of aromatic nitro-amines and the prevention of diaryl formation in the Sandmeyer reaction

Hodgson, Herbert H.; Walker, John

doi:10.1039/jr9330001620

Cited by 63 publications

(25 citation statements)

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“…In section 4.4 the synthesis of a more stable methoxy functionalized precursor will be discussed on which some chlorine free acids as sulfuric acid and hydroiodic acid can be used for the Sandmeyer reaction. [281][293] [294] The palladium catalyzed coupling reaction of aryl hydrazides with aryl halides followed by direct oxidation is shown in Scheme 34 and is envisaged as strategy for a cyclization together with an azo formation. [35] [186] Tert-butyl carbazate (Bochydrazine, A2) is first cross coupled with an aryl halide A1 and then further treated with another aryl halide A4 to form the diphenylhydrazine intermediate A5 which is then oxidized to the azobenzene derivative A6.…”

Section: Palladium Catalyzed Azo Formationmentioning

confidence: 99%

Shape‐Switchable Azo‐Macrocycles

et al. 2009

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The synthesis of four shape‐switchable macrocycles comprising different peripheral substituents is described. The macrocycles 1–4 consist of m‐terphenyl semicircles interlinked by two azo joints. These macrocycles were assembled from nitro‐functionalized m‐terphenyl moieties through reductive dimerization. The semicircles were assembled through Suzuki cross‐coupling reactions. The molecular weights of the macrocycles were determined by vapour pressure osmometry, because mass spectrometry failed in the cases of 2 and 3. The E → Z photoisomerization reactions were analysed by UV/Vis spectroscopy complemented by 1H NMR studies. A very slow thermal back‐reaction indicated considerable stabilization of the Z isomer. The reduced efficiency of the thermal back‐reaction probably arises from the reduced degree of freedom due to the mechanical interlinking of the two azo groups. The photostationary state consisted of all‐Z (85 %) and all‐E isomers (15 %). The E → Z transformation induced by irradiation displayed simple exponential kinetics, which indicates pairwise switching of the two azo groups in a macrocycle, at least on the timescale under investigation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Palladium Catalyzed Azo Formationmentioning

confidence: 99%

Shape‐Switchable Azo‐Macrocycles

et al. 2009

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“…5-Chtoro-1-naphthol was synthesized by the method of Erdmann & Kirchhoff (1888). It was also prepared from 5-nitro-1-chloronaphthalene (Hodgson & Walker, 1933) by reduction to 5-chloro-1-naphthylamine followed bydiazotization and hydrolysis of the diazonium group.…”

mentioning

confidence: 99%

“…8-Chtmo-1-naphthol was synthesized from 8-nitro-1-naphthylamine (prepared by the method of Hodgson & Davey, 1939), by replacement of the amino group by chlorine using the procedure of Hodgson & Walker (1933), followed by reduction to 8-chloro-l-naphthylamine, diazotization and hydrolysis of the diazonium group. (8-Chloro-1-naphthol could not be obtained by the hydrolysis of 8-nitro-1-chloronaphthalene with boiling water as reported by Woroshtzow & Koslow (1936) …”

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confidence: 99%

The Decomposition of 1-Chloro- and 1-Bromonaphthalene by Soil Bacteria

Walker

Wiltshire

1955

Journal of General Microbiology

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SUMMARY: Two species of naphthalene-utilizing bacteria from soil were able to metabolize 1-chloro-and 1-bromonaphthalene. From cultures in which l-chloronaphthalene was the sole source of organic carbon, D-8-ChlOrO-1: 2-dihydro-1 : 2-dihydroxynaphthalene and 3-chlorosalicylic acid were isolated. 3-Bromosalicylic acid was isolated from cultures with 1-bromonaphthalene and evidence of the formation of a 'diol' compound obtained. The course of the metabolic pathways is discussed.

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“…Le 1-chloro-et le 1-bromo-4-nitronaphtalitne, le 1-chloro-et le 1-bromo-2-nitronaphtalPne ainsi que le 2-chloro-1-nitronaphtalitne ont 6t6 pritparits selon IHodgson et Wallier (11). Ces cornposits cristallisent beaucoup mieux dans la ligroine (Eb = 65-110") que dans 116thanol tel que suggitrit.…”

Section: P a R T I E E S P E R I M E N T A L E~unclassified

Contribution À l'ÉTUDE De La Réaction De Von Richter: Iii. Sur La Réaction Avec Divers Nitronaphtalènes

Cullen¹,

L'Écuyer²

1961

Can. J. Chem.

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Dans la reaction de von Richter avec les deriv6s du naphtalkne, le rendement des acides naphtoiques form& est nettement inferieur i celui des acides benzoi'ques obtenus dans la serie du benzkne. P a r contre, des aminoamides se trouvent parmi les produits de la reaction et, lorsque celle-ci est executee dans des conditions bien dkfinies avec le 1-nitronaphtalkne ou le 1-chloro-4-nitronaphtalkne, deux substances, C22H1603N4 e t C Z Z H I~O~N~. C I~ peuvent &tre isolees. Ces dernikres pourraient &tre des intermediaires de la reaction, puisqu'elles se transforment respectivement en acides 2-naphtoi'que e t 4-chloro-2-naphtoi'que, lorsqu'elles sont traitees selon les conditions de la reaction de von Richter.

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382. The diazotisation of aromatic nitro-amines and the prevention of diaryl formation in the Sandmeyer reaction

Cited by 63 publications

References 0 publications

Shape‐Switchable Azo‐Macrocycles

Shape‐Switchable Azo‐Macrocycles

The Decomposition of 1-Chloro- and 1-Bromonaphthalene by Soil Bacteria

Contribution À l'ÉTUDE De La Réaction De Von Richter: Iii. Sur La Réaction Avec Divers Nitronaphtalènes

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