Synthesis and crystal structure of 2,2′-dimethyl-8,8′-biquinolyl

Kitamura, Chitoshi; Yamamoto, Shinya; Ouchi, Mikio; Yoneda, Akio

doi:10.3184/030823400103165662

Cited by 4 publications

(3 citation statements)

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“…The bond distances and bond angles are presented in table 2 and their values were found in good agreement with some analogous structures (Abboud et al 1990;Reboul et al 1993;Sekine et al 1994;Rajnikant et al 1995;Nieger et al 1998;Kitamura et al 2000;Pilati et al 2001).…”

Section: Resultssupporting

confidence: 79%

X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

2004

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The crystal structure of 3,3′ ′-dimethoxybiphenyl has been determined by X-ray diffraction methods with an aim of describing the hydrogen interaction in biphenyl derivatives. The title compound crystallizes in monoclinic space group P2 1 /c with unit cell dimensions, a = 7⋅ ⋅706(1), b = 11⋅ ⋅745(2), c = 12⋅ ⋅721(2) Å, β β = 92⋅ ⋅31(1)°, Z = 4 and its structure has been refined up to the reliability index of 3⋅ ⋅8%. The average torsion angle about the interring CC bond is 37⋅ ⋅5°. The O1 and O1′ ′ atoms of the methoxy group are deviated by 0⋅ ⋅046(1) Å and 0⋅ ⋅234(1) Å from the mean planes of respective rings. The crystal cohesion is pronounced due to three-intermolecular C-H… …O hydrogen bonds.

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Section: Resultssupporting

confidence: 79%

X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

2004

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“…8,8‘-Biquinolyls have been previously prepared by metal-mediated reductive dimerization of 8-haloquinolines; for example, see ref c,d.…”

Section: Referencesmentioning

confidence: 99%

“…In connection with a new research program, we required synthetic entry to symmetric 8,8‘-biquinolyl derivatives, such as 1a − c , equipped with metal ion chelating substructure at C6−C7‘ and C6‘−C7‘ (Figure ) . 8,8‘-Biquinolyls constitute a little known class of biaryl molecules, and a survey of the literature revealed a paucity of suitable methods for their preparation . Pertinent to our problem, there were no reported examples of 8,8‘-biquinolyls which possessed oxygenation at C7 and C7‘.…”

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confidence: 99%

Harnessing Anionic Rearrangements on the Benzenoid Ring of Quinoline for the Synthesis of 6,6‘-Disubstituted 7,7‘-Dihydroxy-8,8‘-biquinolyls

2004

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7,7'-Bis(((dimethylamino)carbonyl)oxy)-8,8'-biquinolyl (5) was prepared in 71% yield by regioselective directed ortho metalation (DoM) of N,N-dimethyl O-quinol-7-yl carbamate (2) with LDA followed by oxidation with anhydrous ferric chloride. DoM of 5 with excess LDA induced double anionic ortho-Fries rearrangement and gave 6,6'-bis((dimethylamino)carbonyl)-7,7'-dihydroxy-8,8'-biquinolyl (8). Treatment of N,N-diethyl O-(8-iodoquinol-7-yl) carbamate (16) with LDA in THF solvent at -78 degrees C, followed by addition of anhydrous ferric chloride, resulted in an efficient tandem halogen-dance dimerization process which afforded 7,7'-bis(((diethylamino)carbonyl)oxy)-6,6'-diiodo-8,8'-biquinolyl (17) directly in 54% yield.

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Cu,Ni, andPdMediated Homocoupling Reactions in Biaryl Syntheses: TheUllmann Reaction

Nelson

Crouch

2004

Organic Reactions

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The traditional Ullman reaction is the homocoupling of aromatic halides mediated by copper at elevated temperatures. Ullman first reported this reaction in 1901. Although the coupling conditions first reported are still widely used, a host of modifications have been made to these reactions. Some of these modifications include the use of activated and alternative metals, often resulting in much lower coupling temperatures. Nickel and palladium are the most utilized source of alternative metals, Periodic reviews have been published. This chapter covers the literature on copper, nickel, and palladium mediated homocoupling reactions in biaryl synthesis from 1901 to 2000. The focus of this chapter is the scope and limitation of these processes, preparation of the activated metal, and mechanism of the homocoupling process

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Synthesis and crystal structure of 2,2′-dimethyl-8,8′-biquinolyl

Abstract: 2,2′-Dimethyl-8,8′-biquinolyl was prepared by homo-coupling and its structure was first elucidated by X-ray analysis.

Cited by 4 publications

References 5 publications

X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

Harnessing Anionic Rearrangements on the Benzenoid Ring of Quinoline for the Synthesis of 6,6‘-Disubstituted 7,7‘-Dihydroxy-8,8‘-biquinolyls

Cu,Ni, andPdMediated Homocoupling Reactions in Biaryl Syntheses: TheUllmann Reaction

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