Bulletin of the Chemical Society of Japan p. 845 - 851 (1982)
Update date:2022-08-05
Topics: Preparation Conformational Properties
Ibuki, Eiichi
Ozasa, Shigeru
Fujioka, Yasuhiro
Mizutani, Hiroshi
Six new 1,8-diarylnaphthalenes, each having closely held parallel aromatic rings, were synthesized by a Kharash-type Grignard cross-coupling of arylmagnesium iodide and 1,8-diiodonaphthalene in the presence of N,N'-bis(1-methyl-3-oxobutylidene)ethylenediaminatonickel(II) as a catalyst.Among them, 1,8-di(1-naphthyl)naphthalene was obtained as cis and trans rotamers, caused by the restricted rotation at the 1,8-position.Interconversion between the rotamers on heating above their melting points was confirmed by differential scanning calorimetry.The proton magnetic resonance spectral studies of the 1,8-diarylnaphthalenes indicated the presence of a face-to-face arrangement of aromatic rings in the peri-position.Two new 8,8'-diaryl-1,1'-binaphthyls, each having two sets of closely held parallel aromatic rings, were isolated as minor coupling products.Trans-trans conformations were proposed for them on the basis of their thermal behavior.Several nickel(II) complexes were found to be effective catalysts for preparative Grignard cross-coupling reaction involving closely crowded geometry.
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