J. Chem. Soc., B:

1969

DOI: 10.1039/j29690000523

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Applications of proton resonance spectroscopy to problems of organic chemistry. Part XXX. 1,2-Dihydronaphthalenes

Alan R. Katritzky²,

Frank C. Pennington³

et al.

Abstract: N.m.r. spectra indicate that 1.2-dihydronaphthalene and its 4-phenyl derivative are in mobile equilibrium. Substituents in the 1 -position are shown to exist preferentially ' pseudo-axial ' by a detailed study of coupling constants of dihydronaphthalenes and related model compounds.University of East Anglia, Norwich BUTCHER 2 analysed the microwave spectrum of cyclohexa-1'3-diene and estimated the angle of torsion between the 1,2-and 3'4-bonds as 17.5 & 2". Earlier, Beckett and Mulley suggested that 9 10-dihyd… Show more

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Bestrahlungen Von L-hhyl-l2-dihydronaphtalin1

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“…Das Destillat (100 mg, 24%) wies im KGC. folgende Zusammensetzung auf: 4,0% cis, cis ll,Syo trans,9,[2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] (19) identifiziert. Fraktion I (kiirzeste gas-chromatographische Retentionszeit) wurde bei 80-85'/ 12 Torr destilliert.…”

Section: Bestrahlungen Von L-hhyl-l2-dihydronaphtalinunclassified

“…Die ihren NMR.-Spektren entnommenen cheinischen Verschiebungen und Kopplungen sind in Tabelle 1 zusammengestellt (vgl. hierzu [14]). Die charakteristischen Randen ihrer 1R.-Spektren (vgl.…”

unclassified

“…2 ) stinimen mit den Spektren vergleichbarer 1,2-Dihydronaphtaline gut uberein r151. (2,60), 262 (3,98), 257 (3,99), 221,5 (4,24), 215 (4,37), 209,5 (4,34) 294 S (2,57), 264 (3,98), 257,5 (4,00), 222 (4, 27), 215 (4,41), 210 (4,37) 293 S (2,63), 262,5 (4,07), 257 (4,06), 222 (4, 28), 215 (4,43), 209,5 (4,40) 295 (2,72), 260 (3,97), 223,5 (4,17), 216,5 (4,35), 294 (2,73), 262 (4,01), 257 (4,00), 221, 5 (4,19), 215 (4,36), 210 (4,32) 296 (2,82), 270 (4,08), 262 (4,09), 225 (4, 14), 218,5 (4,29), 213 (4, 32) 293 (3,00), 265 S (3,91), 259 (3,94), 223 (4,21), 216,5 (4,32), 211 (4,27) 211, (4, 33) 230,s (3,33), 219,5 (4,19), 212 (4, 33) 231 (3,33), 220 (4, 23), 212 (4,40) 230,5 (3,…”

unclassified

“…1 ..5. 2,2-Dimethyl-l,2-dihydronaphtalin(14) (vgl. , 131).-3 , 3 -/~7 M Z e t h~~-/ -~e t~~t~I )~2 .~\-ui-Clc nach r13j clurch Grigimvd-Addition von 30 g (0,24 Mol) Benzylchlorid ( F l u k n , puriss.)…”

unclassified

“…: s. Tabelle 5. MS. : 158 (Mf,12), 143(16), 141 (7), 130(14), 129 (loo), 128 (50), 127(18), 115(13), 102 (6), 91 (4), 77(7), 70,5 (4). Das zweite Produkt (26,1%) wurde bei 95-100°/10 Torr destilliert; es wurde als 2-Propyl-allenyZbenzoZ(21) erkannt.…”

unclassified

See 4 more Smart Citations

Photochemisches Verhalten von 1‐ und 2‐alkylierten 1,2‐Dihydronaphtalinen

¹

,

²

,

³

et al. 1971

Helvetica Chimica Acta

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Irradiation of 1-alkyl-substituted 1,2-dihydronaphthalenes (10, 11, 12) with a lowpressure mercury lamp yields by ring opening w-vinyl-o-quinodimethanes, which undergo [l, 71 H-shifts to give 1,2-divinyl-benzenes (8, 18, 23; cf. schemes 2 , 3 and 4). In a further photoreaction of the divinylbenzenes, benzobicyclo[3.l.0]hex-2-enes (17,19,22) are formed. Z-f~lkyl-suhstit~ited 1,2-dihydronaphthalenes (13, 14, 15, 16) are transformed by irradiation into o-vinyl-o-quinoclimethanes, which show [l, 71 H-shifts to yield in this case 2-(buta-l', 3'-dienyl)-toluencs (9, 25, 26, 27; cf. schemes 6 and 7). The irradiation of 1-methyl-(10) and 1-ethyl-1,2-dihydronaphthalene (11) with a high-pressure mercury lamp produces, besides the products of irradiation using the lowpressure lamp, 2-ethyl-allenylbenzene (24), and (from 11) 4-exo-ethyl-benzobicyclo[3.1.0]hex-2ene (exo-20) and 2-propyl-allenylbenzenc (21), respectively (cf. scheme 5). Obviously, these products arise from a photoreaction of thc primarily formed w-vinyl-o-quinodimethanes a. 5 1 R -6 7 8 9 2. Herstellung der 1,2-Dihydronaphtaline. ~ k-ur die photocheniischen Versuclir wurden die in Formelschema 1 aufgefiihrten 1,Z-Dihydronaphtaline hergestellt. 10, 11, 13, 15 und 16 wurden nach Standardniethoden iiber eine Malonesterkondensation iiiit den entsprechenden I'l~envlalkvll~roiiiiden gemass dem fur die Synthese HELVETICA C H I M I C~ -\CTA 1-01 54, Fasc 7 (1971) ~ Nr. 256 231 5 von 11 wiedergegebenen Reaktionsschema gewonnen. Die analoge Herstellung von 15 und 16 ist in der Literatur beschrieben (vgl. [lo] bzw. [ll]). 4. PPS 5. LiAlH4 ~~~~~~ 9 -6. H3P04 COOH 1. CHZ (COOCZH5)2 11 PPS = Polyphosphorsaure Formelschema 1 10 11 12 C03 C03 ii6 -12 13 14 15 16Die Alkylierungen des Malonsaure-diathylesters waren in allen Fallen von Bromwasserstoffeliminierungen begleitet, so dass die Ausbeuten an alkylierten Malonsaure-diathylestern in der Regel 50% nicht uberstiegen. Die Herstellung von 15 gelang nur iiber die Methylierung des nach dem ersten Schritt erhaltenen /3-Phenylisopropylmalonsaure-diathylesters (vgl. [lo]). Versuche, Methylmalonsaure-diathylester direkt mit P-Phenylisopropylbromid zu alkylieren, fuhrten ausschliesslich zur Rroinwasserstoffabspaltung aus dem Bromid.Bei der Wasserabspaltung aus den entsprechenden 1-Tetralolen mit 85-proz. Phosphorsaure bei 110" traten stets auch die entsprechenden Naphtaline in Mengen his zu 10% auf 2). Die Naphtaline liessen sich leicht durch Chroniatographie der Reaktionsprodukte an Kieselgel, das niit 10% Pikrinsaure beladen war, mittels Elution mit Pentan entfernen. 2,Andere Wasserabspaltungsmethoden, z . B . Phosphoroxychlorirl/Pyridin, lieferten grosserc Mengen der Naphtaline. 13 und 15 wurden aus den entsprechenden LTetralolen durch Erhitzen mit 9-Toluolsulfonsaurechlorid/Pyridin im Eombenrohr auf 140" gewonnen. 231r1 HI~LVRTIC.\ ( ' H I M I C A ,\(:TA ~ \-ol. 54, 1;asc. 7 (1971) -. XI-. 250 1 0 -2~) rnit einer Niederdrucklampe bestrahlt. Es entstehen wieder die Photoprodukte exo-17 und endo-17, wobei exo-17 mengenmassig iiber...

“…Das Destillat (100 mg, 24%) wies im KGC. folgende Zusammensetzung auf: 4,0% cis, cis ll,Syo trans,9,[2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] (19) identifiziert. Fraktion I (kiirzeste gas-chromatographische Retentionszeit) wurde bei 80-85'/ 12 Torr destilliert.…”

Section: Bestrahlungen Von L-hhyl-l2-dihydronaphtalinunclassified

“…Die ihren NMR.-Spektren entnommenen cheinischen Verschiebungen und Kopplungen sind in Tabelle 1 zusammengestellt (vgl. hierzu [14]). Die charakteristischen Randen ihrer 1R.-Spektren (vgl.…”

unclassified

“…2 ) stinimen mit den Spektren vergleichbarer 1,2-Dihydronaphtaline gut uberein r151. (2,60), 262 (3,98), 257 (3,99), 221,5 (4,24), 215 (4,37), 209,5 (4,34) 294 S (2,57), 264 (3,98), 257,5 (4,00), 222 (4, 27), 215 (4,41), 210 (4,37) 293 S (2,63), 262,5 (4,07), 257 (4,06), 222 (4, 28), 215 (4,43), 209,5 (4,40) 295 (2,72), 260 (3,97), 223,5 (4,17), 216,5 (4,35), 294 (2,73), 262 (4,01), 257 (4,00), 221, 5 (4,19), 215 (4,36), 210 (4,32) 296 (2,82), 270 (4,08), 262 (4,09), 225 (4, 14), 218,5 (4,29), 213 (4, 32) 293 (3,00), 265 S (3,91), 259 (3,94), 223 (4,21), 216,5 (4,32), 211 (4,27) 211, (4, 33) 230,s (3,33), 219,5 (4,19), 212 (4, 33) 231 (3,33), 220 (4, 23), 212 (4,40) 230,5 (3,…”

unclassified

“…1 ..5. 2,2-Dimethyl-l,2-dihydronaphtalin(14) (vgl. , 131).-3 , 3 -/~7 M Z e t h~~-/ -~e t~~t~I )~2 .~\-ui-Clc nach r13j clurch Grigimvd-Addition von 30 g (0,24 Mol) Benzylchlorid ( F l u k n , puriss.)…”

unclassified

“…: s. Tabelle 5. MS. : 158 (Mf,12), 143(16), 141 (7), 130(14), 129 (loo), 128 (50), 127(18), 115(13), 102 (6), 91 (4), 77(7), 70,5 (4). Das zweite Produkt (26,1%) wurde bei 95-100°/10 Torr destilliert; es wurde als 2-Propyl-allenyZbenzoZ(21) erkannt.…”

unclassified

See 3 more Smart Citations

Photochemisches Verhalten von 1‐ und 2‐alkylierten 1,2‐Dihydronaphtalinen

¹

,

²

,

³

et al. 1971

Helvetica Chimica Acta

View full text Add to dashboard Cite

Irradiation of 1-alkyl-substituted 1,2-dihydronaphthalenes (10, 11, 12) with a lowpressure mercury lamp yields by ring opening w-vinyl-o-quinodimethanes, which undergo [l, 71 H-shifts to give 1,2-divinyl-benzenes (8, 18, 23; cf. schemes 2 , 3 and 4). In a further photoreaction of the divinylbenzenes, benzobicyclo[3.l.0]hex-2-enes (17,19,22) are formed. Z-f~lkyl-suhstit~ited 1,2-dihydronaphthalenes (13, 14, 15, 16) are transformed by irradiation into o-vinyl-o-quinoclimethanes, which show [l, 71 H-shifts to yield in this case 2-(buta-l', 3'-dienyl)-toluencs (9, 25, 26, 27; cf. schemes 6 and 7). The irradiation of 1-methyl-(10) and 1-ethyl-1,2-dihydronaphthalene (11) with a high-pressure mercury lamp produces, besides the products of irradiation using the lowpressure lamp, 2-ethyl-allenylbenzene (24), and (from 11) 4-exo-ethyl-benzobicyclo[3.1.0]hex-2ene (exo-20) and 2-propyl-allenylbenzenc (21), respectively (cf. scheme 5). Obviously, these products arise from a photoreaction of thc primarily formed w-vinyl-o-quinodimethanes a. 5 1 R -6 7 8 9 2. Herstellung der 1,2-Dihydronaphtaline. ~ k-ur die photocheniischen Versuclir wurden die in Formelschema 1 aufgefiihrten 1,Z-Dihydronaphtaline hergestellt. 10, 11, 13, 15 und 16 wurden nach Standardniethoden iiber eine Malonesterkondensation iiiit den entsprechenden I'l~envlalkvll~roiiiiden gemass dem fur die Synthese HELVETICA C H I M I C~ -\CTA 1-01 54, Fasc 7 (1971) ~ Nr. 256 231 5 von 11 wiedergegebenen Reaktionsschema gewonnen. Die analoge Herstellung von 15 und 16 ist in der Literatur beschrieben (vgl. [lo] bzw. [ll]). 4. PPS 5. LiAlH4 ~~~~~~ 9 -6. H3P04 COOH 1. CHZ (COOCZH5)2 11 PPS = Polyphosphorsaure Formelschema 1 10 11 12 C03 C03 ii6 -12 13 14 15 16Die Alkylierungen des Malonsaure-diathylesters waren in allen Fallen von Bromwasserstoffeliminierungen begleitet, so dass die Ausbeuten an alkylierten Malonsaure-diathylestern in der Regel 50% nicht uberstiegen. Die Herstellung von 15 gelang nur iiber die Methylierung des nach dem ersten Schritt erhaltenen /3-Phenylisopropylmalonsaure-diathylesters (vgl. [lo]). Versuche, Methylmalonsaure-diathylester direkt mit P-Phenylisopropylbromid zu alkylieren, fuhrten ausschliesslich zur Rroinwasserstoffabspaltung aus dem Bromid.Bei der Wasserabspaltung aus den entsprechenden 1-Tetralolen mit 85-proz. Phosphorsaure bei 110" traten stets auch die entsprechenden Naphtaline in Mengen his zu 10% auf 2). Die Naphtaline liessen sich leicht durch Chroniatographie der Reaktionsprodukte an Kieselgel, das niit 10% Pikrinsaure beladen war, mittels Elution mit Pentan entfernen. 2,Andere Wasserabspaltungsmethoden, z . B . Phosphoroxychlorirl/Pyridin, lieferten grosserc Mengen der Naphtaline. 13 und 15 wurden aus den entsprechenden LTetralolen durch Erhitzen mit 9-Toluolsulfonsaurechlorid/Pyridin im Eombenrohr auf 140" gewonnen. 231r1 HI~LVRTIC.\ ( ' H I M I C A ,\(:TA ~ \-ol. 54, 1;asc. 7 (1971) -. XI-. 250 1 0 -2~) rnit einer Niederdrucklampe bestrahlt. Es entstehen wieder die Photoprodukte exo-17 und endo-17, wobei exo-17 mengenmassig iiber...

Electrocarboxylation of Carbon Dioxide with Polycyclic Aromatic Hydrocarbons Using Ni as the Cathode

¹

,

²

,

³

et al. 2010

Chin. J. Chem.

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Using Ni cathode and Al sacrificial anode, the electrocarboxylation of polycyclic aromatic hydrocarbons (naphthalene, 5-methylnaphthalene, anthracene, phenanthrene and 1H-indene) with carbon dioxide (4 MPa) could be successfully performed in an undivided cell containing n-Bu 4 NBr-DMF supporting electrolyte with a constant current at room temperature, affording the corresponding trans-dicarboxylic acids in good to excellent yields (62%-90%). Among the examined cathode materials (Ni, Pt, Ag, Cu and Zn), Ni and Pt cathodes exhibited a good catalytic activity for the electrocarboxylations. In addition, the experimental results indicated that electrolytic conditions (conducting salts, electricity, CO 2 pressure and temperature) could also affect the result of the electrocarboxylation. According to the results of the electrocarboxylations and CV (cyclic voltammetry), a possible electrochemical reaction mechanism was also proposed.

Temperature and solvent variation of the ¹³C and ¹H NMR spectra of r‐1,t‐2,c‐3,t‐4‐tetrachlorotetralin

¹

,

²

,

³

et al. 1982

Org. Magn. Reson.

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Vicinal coupling constants in the 'H and "C NMR spectra of rcl,t-2,~-3,t-4-tetrachlorotetraIii change with temperature and solvent in a manner better explained by conformational equilibration than by intramolecular or solvent-determined distortions.The N M R spectrum of a compound which in solution can exist in more than one conformation in rapid equilibrium is characteristically intermediate between those of the individual conformers, so that the composition of such conformational mixtures can be determined if the spectral parameters of these conformers can be estimated.' Vicinal coupling constants have often been used for this purpose.'" In some cases, the spectral properties of the individual conformers can be determined but, more often, they have to be estimated either from known analogies or by long extrapolations. Idealized geometries have usually to be assumed, and it has been recognized4 that intramolecular distortions could produce angle changes which would be reflected by changes in these parameters, simulating changes in the proportions of the conformers. Weak association between solvent and solute can also change observed chemicalThe use of such measurements to calculate proportions of conformers suffers from a further difficulty, because structural factors affect the relationship between coupling constant, dihedral angle and bond angle.9-'3We have previously discussed the 'H and 13C N M R spectra of a number of isomeric or substituted 1,2,3,4-tetrachlorotetralins.14~1s For these compounds, as for cyclohexenes,16 conformational equilibria rapid on the N M R time-scale persist to quite low temperatures, and the observation of the spectra of two conformers separately, possible for some systems," is not practicable for reasons of solubility. For some of the isomers, the 3-bond coupling constants appear to be intermediate between that expected for either of the half-chair conformations; the results have been treated conventionally to estimate conformational proportions. These calculations are, however, subject to all the uncertainties mentioned above and, consequently, we have sought definite evidence that two conformations coexist in solution in proportions which affect the measured vicinal coupling constants. To do this, we have

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