252. 1-Phenylnaphthalenes. Part I. The synthesis of 2? : 5-dimethoxy-1-phenyl-, 4? : 7-dimethoxy-1-phenyl-, and 1-p-tolyl-7-methyl-naphthalene-2 : 3-dicarboxylic acids

Baddar, F. G.; El-Assal, Lanson S.; Gindy, Munir

doi:10.1039/jr9480001270

Cited by 6 publications

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“…Thus 3a and 3b have been made by dehydrogenating the corresponding cyclohexenylnaphthalenes . Compound 4a was synthesized by oxidizing 6-methyl-4- p -tolyl-1,2-dihydronaphthalene in the presence of selenium at 280 °C, while 5a was obtained from 5-(2-hydroxycyclohexyl)tetralin using ZnCl 2 as a catalyst . Heretofore, products 4a , 4b , or 5a have not been reported to form through thermal dimerization.…”

Section: Resultsmentioning

confidence: 99%

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

and

Verkade

2000

Organometallics

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The alkynes RCtCR (R ) H, Et, Ph), RCtCH (R ) Me(CH 2 ) 5 , Me(CH 2 ) 7 , Ph, Me 3 Si, EtO 2 C), and RCtCR′ (R ) Ph, R′ ) C 6 F 5 ; R ) Me, R′ ) Ph) trimerize to corresponding benzene derivatives in 30-100% yields in the presence of Si 2 Cl 6 as a procatalyst at 170-200 °C over 20-48 h. These reactions represent only the second example of nonmetal-catalyzed alkyne trimerizations. The unsymmetrical alkynes Me 3 SiCtCH, EtO 2 CCtCH, and PhCtCC 6 F 5 gave symmetrical 1,3,5-substituted benzenes, while the others led to isomeric mixtures. A 1:2 molar mixture of PhCtCH and PhCtCPh provided an isomeric mixture (45% yield) consisting mainly of 1,2,4,5-tetraphenylbenzene. While Si 2 (OMe) 6 also catalyzed alkyne trimerizations (though not as efficiently as Si 2 Cl 6 ), Si 2 Me 6 did not, suggesting an electronegativity influence in the formation of the Cl 3 Si • radicals shown to be involved in these reactions. Somewhat unexpectedly, however, neither Si 2 F 6 nor sym-Si 2 Me 2 Cl 4 catalyzed alkyne trimerizations. Experimental support for the radical pathway proposed for the alkyne trimerization observed herein is presented. In the absence of disilane procatalyst, PhCtCH gave an isomeric mixture of dimers, p-MeC 6 H 4 CtCH afforded predominantly a single dimer, and 1-ethynyl-1-cyclohexene provided exclusively a single dimer, whereas RCtCH (R ) alkyl) and PhCtCMe did not react upon heating under the same conditions.

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Section: Resultsmentioning

confidence: 99%

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

and

Verkade

2000

Organometallics

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“…Aryl-substituted butadienes undergo aryl vinyl photocyclizations under oxidative as well as nonoxidative conditions, leading to substituted phenyl naphthalenes or dihydronaphthalenes . To test our hypothesis of 1b being a product of a photochemical 6-π-electron electrocyclization reaction, we irradiated 1a at different wavelengths (250–419 nm) in cyclohexane under an inert atmosphere; formation of 1b , occurring regardless of the wavelength irradiated, was monitored by GC/MS (Table ).…”

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confidence: 99%

Photolability of Per-Arylated Butadienes: En Route to Dihydronaphthalenes

et al. 2014

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Arylated butadienes were prepared employing transition-metal coupling techniques and characterized via UV/vis spectroscopy and X-ray crystal structure analysis. Identification of byproducts led to a photochemical route toward novel multiarylated dihydronaphthalenes. Arylbutadiene-dihydronaphthalene cyclization occurs in solution and in the solid state. Upon substitution of hexaphenylbutadiene, absorption is red-shifted and stability under ambient light is even more reduced.

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“…Substituted-1-arylnaphthalenes were prepared by reaction of a suitably substitutedphenyl Grignard to a suitable a-tetralone as previously described (7,12) to give a substituted-3,4-dihydro-1-arylnaphthalene. The dihydro compound was dehydrogenated with an equivalent amount of 2,3-dichloro-5,6-dicyanobenzoquinone P D Q ) in refluxing benzene for 15 h. The resulting substituted-1-arylnaphthalene was purified by t.1.c.…”

Section: Synthesis Of Substituted-i-arylnaphthalenesmentioning

confidence: 99%

“…(see Experimental). The syntheses of 3a-e and 5a-e were accomplished by the reaction of a-tetralone with the appropriate substitutedphenylmagnesium bromide (7). The first-formed tertiary alcohol was readily dehydrated to give 3,4-dihydro-1-arylnaphthalenes, which were not isolated.…”

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confidence: 99%

Photocyclization reactions of aryl polyenes. The photocychzation of 1-substitutedphenyl-4-phenyl-1,3-butadienes

Leznoff¹,

Hayward²

1970

Can. J. Chem.

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Irradiation of 1-p-substitutedphenyl-4-phenyl-1,3-butadienes gave mixtures of l-p-substitutedphenylnaphthalenes and 7-substituted-1-phenylnaphthalenes. Photocyclization of l-m-substitutedphenyl-4-phenyl-1,3-butadienes gave 1-m-substitutedphenylnaphthalenes, 6-substituted-1-phenylnaphthalenes, and 8-substituted-1-phenylnaphthalenes. Characterization of the photoproducts was achieved through synthesis by an independent method.Canadian Journal of Chemistry, 48,1842 (1970) The photochemical cis-trans isomerization of stilbenes has been extensively investigated in recent years and the detailed mechanism of the reaction has been discussed by several groups (1). The concurrent photochemical cyclizations of stilbene and substituted stilbenes to phenanthrene and substituted phenanthrenes have also been studied both from preparative (2) and mechanistic (3) points of view.' Stilbene-like photochemical cyclizations have recently been utilized in the synthesis of a wide variety of interesting polycyclic compounds (4).Photochemical cyclizationsi of 1,Cdiphenyl-1,3-butadienes have received scant attention since Fonken showed that 1,4-diphenyl-1,3-butadiene undergoes a photochemical cyclization to give I-phenylnaphthalene (5). The present paper describes the photocyclization of l-substitutedphenyl-4-phenyl-l,3-butadienes.The 1 -substitutedphenyl-4-phenyl-1,3-butadienes (la-e and 2a-e) were prepared by one of two possible Wittig reactions (6). Either a solution of triphenylcinnamylphosphonium bromide and a monosubstituted benzaldehyde in methanol was reacted with lithium methoxide (method A) or a solution of cinnamaldehyde and a monosubstitutedbenzylphosphonium halide in methanol was treated with lithium methoxide (method B). Although the yields of these reactions were only moderate (Table I), the ready availability of the starting materials and the simplicity of the reactions favored the use of Wittig reactions in the synthesis of 1,Cdiaryl-1,3-butadienes. 'The photochemical cyclization reaction of stilbenes gives dihydrophenanthrene intermediates, which are very readily oxidized to phenanthrenes. Hence the term "photocyclization" shall include both the cyclization and oxidation steps.Compounds la-e and 2a-e were readily characterized by their spectral data (Table 2) and by comparison with known 1,4-diaryl-1,3-butadienes. Mass spectroscopy revealed the presence of strong parent ions for la-e and 2a-e. The ultraviolet (u.v.) and infrared (i.r.) spectra clearly showed the presence of the butadiene m~i e t y .~ Irradiation of 1 x M solutions of l-psubstitutedphenyl -4 -phenyl -1,3 -butadienes (la-e) in dry benzene containing 2 x M iodine gave, after 3-6 days, mixtures of l-psubstitutedphenylnaphthalenes (3a-e) and 1-phenyl-7-substitutednaphthalenes (4a-e). As shown in eq.[I], photocyclization of la-e can occur to the unsubstituted phenyl ring to give 3a-e and to the substituted phenyl ring to give Similarly, irradiation of I -m -substitutedphenyl-4-phenyl-1,3-butadienes (2a-e) gave mixtures of 1-m-substitutedphenylnaphthalenes ...

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252. 1-Phenylnaphthalenes. Part I. The synthesis of 2? : 5-dimethoxy-1-phenyl-, 4? : 7-dimethoxy-1-phenyl-, and 1-p-tolyl-7-methyl-naphthalene-2 : 3-dicarboxylic acids

Cited by 6 publications

References 0 publications

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

Photolability of Per-Arylated Butadienes: En Route to Dihydronaphthalenes

Photocyclization reactions of aryl polyenes. The photocychzation of 1-substitutedphenyl-4-phenyl-1,3-butadienes

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