1959
DOI: 10.1021/ja01529a043
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Carbonyl Reactions. X. The Acid-catalyzed Isomerization of cis-Benzalacetophenone1,2

Abstract: Tetroxide).-meso-1,2-Dinitro-1,2-diphenylethane (I, 0.1 g., m.p. 225°u ncor.) was stirred for 8 hours in ethyl ether (200 ml.) at 0°c ontaining excess dinitrogen tetroxide. After the mixture had been poured on ice, allowed to stand, washed with water, dried over magnesium sulfate and evaporated.Compound I was recovered essentially quantitatively, m.p. 220-225°; the product was colored by trace amounts of anitrostilbene.

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Cited by 16 publications
(5 citation statements)
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“…To check the value for the hydration−dehydration equilibrium constant ( K 23 ), the hydration reaction of enone was also studied under acidic conditions using HPLC analysis. In acid we expected, ,, and found in this case, that retro-aldol reaction is much slower than hydration−dehydration. The equilibrium constant obtained in this experiment was consistent with that obtained from the base-catalyzed hydration reaction of enone.…”
Section: Resultsmentioning
confidence: 60%
“…To check the value for the hydration−dehydration equilibrium constant ( K 23 ), the hydration reaction of enone was also studied under acidic conditions using HPLC analysis. In acid we expected, ,, and found in this case, that retro-aldol reaction is much slower than hydration−dehydration. The equilibrium constant obtained in this experiment was consistent with that obtained from the base-catalyzed hydration reaction of enone.…”
Section: Resultsmentioning
confidence: 60%
“…The maximum and minimum heights in the final difference Fourier map were found to be 0.368 e/Å -3 (10)q, E = 81.929(2)q, J = 86.4820(10)q; final R 1 and wR 2 are 0.0392 and 0.0905 respectively. The compound exists in stable E-form with respect to the C7=C8 and C27=C28 part [ 12 ]. In the compound, the C1-C6, C29-C34 rings are perfectly planar and the C10-C15, C20-C25 rings deviate significantly from planarity.…”
Section: Resultsmentioning
confidence: 99%
“…During the same time interval, an increase in absorption at A.=262nm could be observed, thus indicating the formation of cis-chalcone in the trans-->cis photoisomerization process. 5 Lutz and Jordan 4 observed thermally initiated cis-> trans isomerization of chalcone in the presence of H + ions in an isooctane solution.…”
Section: Resultsmentioning
confidence: 99%