Säurekatalysierte Dienon‐Phenol‐Umlagerungen von 6‐Propargyl‐6‐methyl‐cyclohexa‐2,4‐dien‐1‐onen; ladungskontrollierte, aromatische [1s, 2s]‐ und [3s, 4s]‐sigmatropische Reaktionen

Widmer, Ulrich; Hansen, Hans‐Jürǵen; Schmid, Hans

doi:10.1002/hlca.19730560610

Cited by 16 publications

References 13 publications

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Dienone‐Phenol Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The dienone‐phenol rearrangement is, in most cases, the transformation of 4,4‐disubstituted cyclohexadienone into a 3,4‐disubstituted phenol upon treatment of acid; however, 2,2‐disubstituted cyclohexadienone and cyclohexadienone with exocyclic double bond can also be converted into the corresponding disubstituted phenol under similar conditions. It has been reported that the driving force for all of these rearrangements is aromatization. It has been found that the reaction media have strong effects on the rearrangement and the regioselectivity is completely controlled by the electronic factors. The migration tendency of groups at either 4,4 position or 2,2 position has been analyzed using different acid‐promoted conditions. The importance of this reaction has been evidenced in the preparation of steroids, anthracene, phenanthrene, and a variety of phenols.

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Dienone‐Phenol Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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Sigmatrope Verschiebungen bei Allenoxid‐Umlagerungen: der erste allgemeine Zugang zu [3,4]‐Verschiebungen in aliphatischen in Systemen

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Cao

1997

Angewandte Chemie

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Sigmatropic Shifts in Allene Oxide Rearrangements: First General Route to [3,4] Shifts in Aliphatic Systems

Erden

Cao

1997

Angew. Chem. Int. Ed. Engl.

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COMMUNICATIONS 390 nm is absent in the crystals, the intramolecular hydrogen bond of the dye within the complex is not perturbed by the cyclic oligosaccharide host.The dye-trapping process in aqueous solution can also be monitored by the biphasic behavior of the fluorescence intensity at 390 nm as a function of p-CD concentration. Thus, at low concentrations of p-CD the intensity of this band initially increases ( Figure 2B) due to protection of the emitting fluorophore by p-CD. This trend is reversed and the intensity starts to decline upon further increase of the oligosaccharide concentration, with the simultaneous appearance of the band at 550 nm, as noted above. The BH analysis of the initial change of the intensity at 390 nm yields a 1 : 1 stoichiometry and a binding constant K , = 500 M-' The equilibrium constant K2 of the 1 :2

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Säurekatalysierte Dienon‐Phenol‐Umlagerungen von 6‐Propargyl‐6‐methyl‐cyclohexa‐2,4‐dien‐1‐onen; ladungskontrollierte, aromatische [1s, 2s]‐ und [3s, 4s]‐sigmatropische Reaktionen

Abstract: Summary. The acid catalysed dienone-phenol rearrangement of methyl substituted o-propargylcyclohexadienones (scheme 3) was investigated.

Cited by 16 publications

References 13 publications

Dienone‐Phenol Rearrangement

Dienone‐Phenol Rearrangement

Sigmatrope Verschiebungen bei Allenoxid‐Umlagerungen: der erste allgemeine Zugang zu [3,4]‐Verschiebungen in aliphatischen in Systemen

Sigmatropic Shifts in Allene Oxide Rearrangements: First General Route to [3,4] Shifts in Aliphatic Systems

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