Die Molekülschwingungs‐Spektren des Naphthalins und seiner Derivate, I. Mitteil.: Darstellung deuterierter Naphthaline und ihre Raman‐Spektren

Goubeau, J.; Luther, Horst; Feldmann, Klaus; Brandes, Günter

doi:10.1002/cber.19530860216

Cited by 17 publications

(3 citation statements)

References 11 publications

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“…Care had to be taken to avoid chlorinolysis to perchloroindan which occurs easily at higher temperatures [246]. Goubeau used Schwemberger's method, completing the chlorination by treatment with antimony pentachloride [247]. Brintzinger and Orth realized the perchlorination in the vapour phase using charcoal (400°), rhodium trichloride-silica (400-480°), or rhodium trichloride-alumina (400°) [31] in nearly quantitative yields.…”

Section: Perchloronaphthalene: Synthesesmentioning

confidence: 99%

Aromatic and Alkaromatic Chlorocarbons

Ballester

Olivella

1974

Polychloroaromatic Compounds

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Section: Perchloronaphthalene: Synthesesmentioning

confidence: 99%

Aromatic and Alkaromatic Chlorocarbons

Ballester

Olivella

1974

Polychloroaromatic Compounds

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“…The synthetic methods is the first method in preparation of benzene-d 6 . Benzene-d 6 has been prepared by the polymerization of acetylene-d 2 [1], but is difficult to purify because of numerous other products. The second preparation of benzene-d 6 was used of H/D exchange reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectral Analysis of Benzene-d<sub>6</sub>

Guo¹,

She²,

Ning³

et al. 2014

AMR

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“…Monodeuteriated naphthalene, methyl naphthalene and ethylnaphthalene had previously been prepared from the bromo derivatives through the Grignard synthesis by GOUBEAU, LUTHER, FELDMANN and BRANDES [2]. Octadeuterionaphthalene is also reported in this paper.…”

mentioning

confidence: 93%

Deuterated organic compounds XXV synthesis of 1, 4, 5, 8‐tetradeuterionaphthalene

Renaud

Leitch

1965

J. Labelled Cpd. Radiopharm.

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SUMMARY1,4,5,8-Tetradeuterionaphthalene was synthesized from 1 ,Cdibromonaphthalene by two methods. In the first method naphthalene was repeatedly brominated in chloroform and then debrominated with zinc dust in alkaline deuterium oxide. In the second, 1,4-dibromonaphthaIene was nitrated to produce 1,4-dibrorno-5-nitronaphthalene which underwent reductive debromination with zinc in alkaline deuterium oxide to l-amino-5,8-dideuterionaphthalene. The latter was converted into l-bromo-5,8-dideuterionaphthalene by a modified Sandmeyer reaction which was brominated to 1,Cdibromo5&dideuterionaphthalene and then debrominated to 1,4,5,8-tetradeuterionaphthalene .In connection with some spectroscopic studies by MITRA and BERNSTEIN which have now been published [l] a number of deuterionaphthalenes were synthesized. Monodeuteriated naphthalene, methyl naphthalene and ethylnaphthalene had previously been prepared from the bromo derivatives through the Grignard synthesis by GOUBEAU, LUTHER, FELDMANN and BRANDES [2]. Octadeuterionaphthalene is also reported in this paper. While our work was in progress SHATENSHTEIN, PEREGUDOV, ISRAILEVICH and KALINACHENKO [3] reported the preparation of 1,4,5,8-tetradeuterionaphthalene by exchanging naphthalene with liquid deuterium bromide at room temperature. Although their extensive studies of the kinetics of aromatic hydrocarbon exchange in liquid deuterium halides constitute an important contribution in this field, serious experimental problems arise in using liquid deuterium halides for preparative exchange reactions.In the present work, we were particulaily interested in obtaining 1,4,5,8-tetradeuterionaphthalene. Our first attempts to prepare this compound were *

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Die Molekülschwingungs‐Spektren des Naphthalins und seiner Derivate, I. Mitteil.: Darstellung deuterierter Naphthaline und ihre Raman‐Spektren

Abstract: Es wird die Darstellung des Oktadeutero‐naphthalins und des Hexadeutero‐benzols sowie von partiell deuterierten Naphthalinen beschrieben; die Raman‐Spektren dieser Verbindungen werden angegeben.

Cited by 17 publications

References 11 publications

Aromatic and Alkaromatic Chlorocarbons

Aromatic and Alkaromatic Chlorocarbons

Synthesis and Spectral Analysis of Benzene-d<sub>6</sub>

Deuterated organic compounds XXV synthesis of 1, 4, 5, 8‐tetradeuterionaphthalene

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