13476-68-1Relevant articles and documents
Two efficient routes to m-terphenyls from 1,3-dichlorobenzenes
Saednya, Akbar,Hart, Harold
, p. 1455 - 1458 (1996)
In the first route 2,6-dichlorophenyllithium (5), prepared by direct lithiation of 1,3-dichlorobenzene, reacted with aryl Grignard reagents to give m-terphenyls in 57-93% yields; the methodology was extended to substituted 1,3-dichlorobenzenes (i.e. 8 → 10). Also, reaction of 5 with MgCl2 gave 2,6-dichlorophenyl-magnesium chloride which, on warming, produced the self-capture product tetrachloro-m-terphenyl 7 in moderate yield. In the second route, reaction of 1,3-dichlorobenzene with excess of aryllithium in diethyl ether at room temperature gave the corresponding m-terphenyls in 59-94% yields. Examples are given in which the aryllithium was prepared by three different routes (ArX + Li, ArX + t-BuLi, ArH + BuLi).
A One-Pot Synthesis of m-Terphenyls via a Two-Aryne Sequence
Du, Chi-Jen Frank,Hart, Harold,Ng, Kwok-Keung Daniel
, p. 3162 - 3165 (2007/10/02)
Aryl-Grignards (3+ equiv) react with 2,6-dibromoiodobenzene or other 1,2,3-trihalobenzenes to give 2,6-diarylphenylmagnesium halides.The mechanism involves Grignard exchange at the central halogen, followed by two cycles of magnesium halide loss and regioselective capture of the resulting aryne by the aryl-Grignard reagent (Scheme I).Typical examples are shown in Table I.The method is especially applicable to m-terphenyls in which the "outer" rings are identical and/or in which substitution at the 2' or other positions of the "central" ring is desired.
Studies of Polyphenyls and Polyphenylenes. II. The Synthesis and Physical Properties of Polyphenyls Containing Para Linkage
Ozasa, Shigeru,Hatada, Noriko,Fujioka, Yasuhiro,Ibuki, Eiichi
, p. 2610 - 2617 (2007/10/02)
Twelwe linear polyphenyls, including quinque- to octiphenyl, were synthesized by the Ullmann cross-coupling reaction of iodobiphenyl with diiodobenzene or iodoterphenyl.Ultraviolet spectral studies of the polyphenyls indicated that the positions of the K-bands above ca.260 nm, regardless of the presence of o- or m-phenylene unit(s), may be considered to be an indication of the approximate number of consecutive p-phenylene units.Infrared studies also showed that the locations of strong or medium bands in the 815-850 cm-1 region may give the same information.The HMO calculations of the longest wavelength absorption bands of twenty-four polyphenyls were carried out.A comparison between the calculated and observed wavelengths gave rather good agreement, except in the cases of two compounds.The signals of the proton magnetic resonanse spectra of eighteen polyphenyls were assigned tentatively.The correlations between the arrangement of the benzene rings and the spectral patterns are discussed.
