Naphthalene analogs

Base-catalyzed condensation of 2-iminoindane-2-carbonitrile (62) with phthalaldehyde affords indeno[2,l-c]-2-benzazepine-5-carbonitrile (63) in excellent yield (95%),97 which is identical to an uncharacterizcd byproduct obtained earlier98 by condensing benzene-1,2-diacetonitrile with phthalaldehyde in the presence of sodium methoxide. The naphthalene analog 64 is prepared by condensing naphthalene-2,3-dicarbaldehyde with the indanecarbonitrile 62 under similar conditions. 

In the presence of KOH, /m(benzotriazol-l-yl)methane 729 reacts with nitrobenzenes to produce />-(/fc (bcnzo-triazol-lyl)methyl]nitrobenzenes 730 (Scheme 114) <1996TL347>. This vicarious nucleophilic substitution of hydrogen <1991S103> can be considered as a convenient way to />-nitrobenzaldehydes 731. Meta and para substituted nitrobenzenes do not react with compound 729 under these conditions, probably due to steric reasons, but 1-nitronaphthalene reacts producing a naphthalene analog of derivative 730. 

Ammonium acetate in acetic acid converts 55a into the imine (59). The hydrogen-bonded, resonance-stabilized form shown is consistent with its high melting point and intense color. The structure is further supported by the ability of the naphthalene analog, which is more soluble, to form a stable complex with cupric perchlorate. ... 

In contrast to 1,1,3,3-tetrachloro-l,3-dihydroisobenzofuran, its naphthalene analog 7 produces only cyclic fluorinated product 8.16... 

Even derivatization of fullerene was achieved by reaction with o-thioquinonemethide 69360 (equation 145). Finally, naphthalene analogs of 69 have been discovered and applied in the preparation of angular systems488 (equation 146). 

The naphthalene analogs of phenols can be placed on the naphthalene nucleus by hydrolyzing the appropriate diazon-ium salt. 

Some information is already in hand to show that such empirical constants are related to more fundamental parameters. Cilento and Berenholc have shown that there is a good linear correlation between f(X) obtained for thyroxine analogs (II) and the negative logarithm of the lifetime of the phosphorescent state (equivalent to the triplet to singlet transition in naphthalene analogs) for the five functions where X = H, CH3, Cl, Br,... 

The two-electron reduction of [Cr(CO)3(r/-arene)j occurs at very negative potentials (e.g., arene = C6H5Me, 1/2 = -2.25 V in MeCN) (84,394,395). The process is irreversible for substituted benzene derivatives but stable dianions, in which the arene is bonded as an r/4-diene, can be generated by electrolytic reduction of the naphthalene analogs (395). 

The treatment of borazine in a silent electric discharge apparatus effects elimination of Hj and coupling of ring units A diphenyl analog, N B Hjo, and a naphthalene analog, NjBjHg, have been identified among the products. 

In order to probe the tolerance of the molybdenum(O) aromatic complexes to electrophilic/acidic environments, a tandem addition sequence was attempted for the complex TpMo(NO)(MeIm)(q -naphthalene) (114) (Fig.25) [17]. In a strategy similar to that used with the TpRe(CO)(MeIm)(q -naphthalene) analog,(see below) an acetonitrile solution (-35 °C) of 114 was exposed sequentially to triflic acid, l-methoxy-2-methyl-l-trimethylsiloxypropene, and an amine base. The 1,2-dihydronaphthalene complex 116 was isolated in virtually quantitative yield. No evidence of free naphthalene or 1,4-addition product was observed. Stirring the reaction mixture with exposure to air resulted in an 80% overall yield of 2-(l,2-dihydro-naphthalen-2-yl)-2-methyl-propinoic acid methyl ester (117) following TLC purification [17]. 

Woollins and co-workers have reported the synthesis of a naphthalene analog of Lawesson s reagent and its subsequent reactions leading to novel phosphorus-containing heterocycles (Scheme 74) <1997CB1485, 1999EJI2327, 1997JCD1347>. 

As shown in Figure 2.2, the condensation of borazine results in a mixture of biphenyl and naphthalene analogs in addition to larger planar units. Like graphitizable pitch, these appear to have the potential to stack in a discotic phase allowing for formation of a graphitic boron... 

Mass spectrometry can also be used in order to gain insight into the mechanism of borazine polymerization. Of particular interest is the means by which polynuclear species such as the naphthalene analog are formed. Examination of the gaseous products reveals that hydrogen is the primary byproduct of the reaction with a small amount of ammonia. 

Styryl and vinyl groups are well known as photochemically and thermally reactive functional groups. Especially, 2-vinylstilbene, ( , )-1,2-distyrylbenzene (3w), and the naphthalene analog (3x) having these reactive groups at orf/to-position of aromatic ring are highly reactive for photochemical dimerization and valence isomerization in solution, even in solid state, and in adsorbed state on silica gel. However, little is known about the cation radical of 3w, probably because the cation radical of 3w is too reactive to afford the identifiable products. 

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