Sodium-ethylenediamine reductive dimerization of naphthalene to 5,6,7,12,13,14-hexahydro-5,13:6,12-dimethanodibenzo[a,f]cyclodecene

Eisenbraun, E. J.; Ansell, L. L.; Dobbs, T. K.; Harris, L. E.; Hertzler, D. V.; Ruehle, P. H.; Burks, John E.; Helm, D. van der

doi:10.1021/jo00879a024

Cited by 3 publications

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“…A sample of II (50 g, 0.31 mol) was stirred with sodium (20 g) and ethylenediamine (700 ml) at 45 °C for 3 h with a stir-shredding device similar to that described for the preparation of hydrocarbon I (Eisenbraun et al, 1976). A similar isolation procedure was used to obtain a crude oil which was distilled (Kugelrohr) to give a fraction boiling at 120°C (0.05 mm) containing mostly 6-methoxytetralin (2.3 g, 4.5%).…”

Section: Synthesismentioning

confidence: 99%

“…The synthesis and crystallographic structure of 5,6,7,12,13,14-hexahydro-5,13 : 6,12-dimethanodibenzo[a,flcyclodecane (I) were recently reported (Eisenbraun, Ansell, Dobbs, Harris, Hertzler, Ruehle, Burks & van der Helm, 1976) as a product obtained from reaction of naphthalene with sodium in ethylenediamine. Obtaining this unusual structure prompted extension of the reaction to 7-methoxy-l,2-dihydronaphthalene (II) in an effort to learn whether methoxylated dimers comparable to hydrocarbon I could be obtained.…”

Section: Introductionmentioning

confidence: 99%

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The structure of a cyclodimer from reaction of 7-methoxy-1,2-dihydronaphthalene with sodium and ethylenediamine. A comparison of bond distances and angles in two molecules

Helm¹,

Ke²,

Ansell³

et al. 1977

Acta Crystallogr Sect B

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6,6 a, 7,12,13, 5 ] cyclohepta [ 1,2-a] n aphth alene, C22H240 z, is a cyclodimerized product obtained from reaction of 7-methoxy-l,2-dihydronaphthalene with sodium and ethylenediamine. The preparation, isolation, and spectral data of this dimer are described.Crystals of the compound are monoclinic, space group P2,/c. The cell dimensions are a = 26.643 (9), b = 8. 165 (3), c = 16.226 (5) A and/~ = 107.56 (2) °. The structure was determined by direct methods and refined with least-squares calculations on 6372 data collected at -160°C. The final R value is 0-060. The asymmetric unit contains two independent molecules which show good agreement of distances for corresponding bonds. It is concluded that the standard deviations calculated from the inverse of the least-squares matrix are not underestimated.

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Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The structure of a cyclodimer from reaction of 7-methoxy-1,2-dihydronaphthalene with sodium and ethylenediamine. A comparison of bond distances and angles in two molecules

Helm¹,

Ke²,

Ansell³

et al. 1977

Acta Crystallogr Sect B

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ChemInform Abstract: SODIUM‐ETHYLENEDIAMINE REDUCTIVE DIMERIZATION OF NAPHTHALENE TO 5,6,7,12,13,14‐HEXAHYDRO‐5,13‐6,12‐DIMETHANODIBENZO(A,F)CYCLODECENE

Eisenbraun¹,

Ansell²,

Dobbs³

et al. 1976

Chemischer Informationsdienst

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Polymerization of aromatic nuclei. XVII. Catalytic hydrogenation of poly(p‐phenylene)

Durham

Kovacic

1977

J. Polym. Sci. Polym. Chem. Ed.

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Hydrogenation of poly(p‐phenylene) (I) in cyclohexane at high temperature and pressure with rhodium catalyst gave, in low yield, oligomers of 1,4‐cyclohexylene(II) in the range of 2–16 cyclohexyl units per chain. Apparently only the low molecular weight fraction in I is reduced because of extreme insolubility. II, which appears to be a novel class, was characterized by molecular weight, 1H‐NMR, 13C‐NMR, and infrared spectra, gas chromatography, and microanalyses. Dicyclohexyl and perhydro‐p‐sexiphenyl served as model compounds for comparison in characterization of II.

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Sodium-ethylenediamine reductive dimerization of naphthalene to 5,6,7,12,13,14-hexahydro-5,13:6,12-dimethanodibenzo[a,f]cyclodecene

Cited by 3 publications

References 4 publications

The structure of a cyclodimer from reaction of 7-methoxy-1,2-dihydronaphthalene with sodium and ethylenediamine. A comparison of bond distances and angles in two molecules

The structure of a cyclodimer from reaction of 7-methoxy-1,2-dihydronaphthalene with sodium and ethylenediamine. A comparison of bond distances and angles in two molecules

ChemInform Abstract: SODIUM‐ETHYLENEDIAMINE REDUCTIVE DIMERIZATION OF NAPHTHALENE TO 5,6,7,12,13,14‐HEXAHYDRO‐5,13‐6,12‐DIMETHANODIBENZO(A,F)CYCLODECENE

Polymerization of aromatic nuclei. XVII. Catalytic hydrogenation of poly(p‐phenylene)

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