1983
DOI: 10.1002/cber.19831160921
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Thermolabile Kohlenwasserstoffe, XX. Synthese, Struktur und Spannung symmetrischer Tetraalkyldiarylethane

Abstract: Die Synthesen von 18 1,1,2,2-Tetraalkyl-l ,Zdiarylethanen 1 -4 durch Dimerisierungsverfahren ausgehend von 10-13 werden beschrieben. Bei fehlenden p-Substituenten X und groBen Alkylseitenketten R' und R2 erhalt man neben oder statt 1 a, p-Dimere 6 oder deren aromatische Folgeprodukte 7. Die Zusammenhange zwischen Spannungsenthalpie H, und Bindungslangen und -winkeln sowie Torsionswinkeln und Rotationspotentialen werden anhand von Kraftfeldberechnungen diskutiert. Zur Absicherung der Kraftfeldmethode wurden zwe… Show more

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Cited by 30 publications
(4 citation statements)
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“…As can be seen in Table , both the strain energy in the scissile bond 9,32 and the remote X-substituent affected the quantum yields (Φ S ) in a way consistent with the proposed mechanism of product formation. The decrease of the donor's homolytic bond strength , (from 1b to 2b to 3b ) resulted in the increase in the quantum yield for destruction of CC. Electron-withdrawing substituents (X) lowered and electron-donating groups increased the quantum yield for disappearance of bicumenes.…”
Section: Discussionmentioning
confidence: 99%
“…As can be seen in Table , both the strain energy in the scissile bond 9,32 and the remote X-substituent affected the quantum yields (Φ S ) in a way consistent with the proposed mechanism of product formation. The decrease of the donor's homolytic bond strength , (from 1b to 2b to 3b ) resulted in the increase in the quantum yield for destruction of CC. Electron-withdrawing substituents (X) lowered and electron-donating groups increased the quantum yield for disappearance of bicumenes.…”
Section: Discussionmentioning
confidence: 99%
“…Materials. 4,4‘-Dimethoxybicumene was prepared by radical-initiated dimerization of 4-methoxycumene according to literature procedures and purified by sublimation to yield a white solid (mp 173−175 °C). 1 H NMR (250 MHz, CDCl 3 ) δ 6.85 (dd, 8H), 3.85 (s, 6H), 1.3 (s, 12 H); 13 C NMR (62.5 MHz, CDCl 3 ) δ 25.3, 43.1, 55.2, 111.9, 129.6, 139.1, 157.3.…”
Section: Methodsmentioning
confidence: 99%
“…As with other 1 2 species [14] and related organic [35,37,38] and organometallic dimers [22,[39][40][41][42][43][44][45][46], the central C-C bond of the present dimers are rather long compared to typical C-C bonds, although not remarkably so given that these are hexasubstituted ethane derivatives. Values of 1.5899 (11) and 1.6194(8) Å are found for the symmetrical and unsymmetrical conformers of 1b 2 , respectively, while a value of 1.6299(13) Å is found for 1h 2 ; these may be compared to hexasubstituted central C-C bond length values of 1.595(5) and 1.601(5) Å for the two inequivalent molecules of the Y = Fc, R = R' = H derivative 1c 2 [14], 1.640(4) Å for the Y = cyclohexyl, R = R' = H derivative 1e 2 [14], 1.573 Å for 2 2 [35], and 1.591 Å for 5 2 [38], while (PhEt 2 C) 2 , a simple hexa-substituted ethane, exhibits a central C-C bond length of 1.635 Å [47]. The tetrasubstituted central C-C bond of 4 2 is also rather long (1.58 Å) [37].…”
Section: Crystal Structuresmentioning
confidence: 99%