Naphthalene 2-phenyl

Fig. 11-6. Calculated adsorption energy of the phenyl group of 1-phenyl naphthalene as a function of the configuration of the adsorbed molecule. Reprinted from the Journal of Physical Chemistry (50) by permission of the American Chemical Society.

Naphthalene, pentamethyl-Naphthalene, 1-phenyl-Naphthalene, 2-phenyl-Naphthalene, 1-propyl-Naphthalene, 2-propyl-Naphthalene, 1,2,3,4-tetrahy dro-1,1,6-trimethyl-... 

Starting with benzene and succinic anhydride and using any other needed reagents, outline a synthesis of 1-phenyl-naphthalene. 

Lithium amides, chiral. Koga et al.x have prepared a series of lithium amides of the type in which one carbon atom adjacent to the nitrogen is chiral and bears a bulky group (phenyl, naphthalene, r-butyl). Highest enantioselective deprotonation... 

Arylnaphthalenes. Arylnaphthalenes can be prepared by replacement of the amino group of naphthylamines by aryl groups. a-Phenyl-naphthalene can be prepared satisfactorily only through the stabilized diazonium salt method, but /3-phenylnaphthalene is obtained readily by several procedures. A considerable number of derivatives of /3-phenylnaphthalene have been prepared. An example is 5-nitro-6-methoxy-2-phenylnaphthalene (XII), which can be obtained in 19% yield from the nitromethoxy-/3-naphthylamine and benzene. From the reaction between diazotized /S-naphthylamine and nitrobenzene and sodium acetate, /S-(2-nitrophenyl)-naphthalene (XIII 14%) and /3-(4-nitrophenyl)-naphthalene (XIV 26%) are formed. 

To 10 g. of the dry salt, well agitated With 30 g. of benzene, at room temperature, are added 3 g. of anhydrous sodium acetate and 1 g. of acetic anhydride. After forty-eight hours, the mixture is heated to 80° until nitrogen ceases to be evolved, the mixture is treated with water, the benzene layer is separated, the solvent is removed, and the a-phenyl-naphthalene is isolated (no details given) yield, 1.4 g. (30%). 

Carbomethoxy- x -phenyl- naphthalene Methyl anthranilate Naphthalene A-l 13... 

A logical next step was the investigations of 2-phenyl-naphthalenes [63]. The archetype structure 24 already showed 13-fold ERp selectivity. Substituents were incorporated at different positions and it was found that specific substitutions at C4 (e.g. 26) or C8 (e.g. 25) resulted in significantly improved ERP selectivity. Substituent... 

Dry distillation of the methohydroxide of CCCLXVI led to a series of optically inactive compounds, the ultraviolet spectra of which resemble that of /S-phenyl naphthalene. They were identified as... 

Sapre and Gates8 (University of Delaware) studied the hydrotreatment of benzene, biphenyl, naphthalene, and 2-phenyl naphthalene over CoO-Mo03/y-Al203... 

Another noteworthy development is an asymmetric synthesis of chiral biaryls by a Pd-catalyzed enantioselective aryl-aryl coupling reaction of prochiral 2,6-bis(triflyloxy)biaryls [62]. Using Cl2Pd[(S)-Phephos] as a chiral catalyst, the first phenylation of l-[2,6-bis(triflyloxy)phenyl]naphthalene with PhMgBr proceeds in 85% ee. As might be expected, the minor enantiomer is the more reactive of the two in the second phenylation. This leads to a kinetic resolution, and the desired monophenylated enantiomer can be obtained in 93% ee. Similarly favorable enantioselective alkynylation results have also been reported [180]. 

Phenylnaphthalene, for example, is obtained in 90% yield when 3,4-dihydro-2-phenyl-naphthalene is boiled for 15 h with chloranil in xylene.129... 

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