Kondensationsreaktionen vom Aldoltypus V. Zur Konfiguration von Derivaten des 2,3-Cyclohexano-(1,3,3)-bicyclononan-2-ol-9-ons

Pitha, Josef; Plešek, Jaromı́r; Horák, M.

doi:10.1135/cccc19611209

Cited by 5 publications

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“…Since 15 is a tertiary alcohol, it is less acidic (Av intermolecular to pyridine = 302 cm-1) than primary alcohols, such as 12 (Av to pyridine = 331 cm-1). This variation in acidity (as well as the positions of the free peaks) helps to explain the spectral shift difference between the comparable bands of 15 (Av = 79 cm-1) and of 12 (Av = 90 cm-1).…”

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Hydrogen bonding. XIX. Intramolecular hydrogen bonding in aliphatic hydroxy ketones

Joris¹,

Schleyer²

1968

J. Am. Chem. Soc.

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confidence: 89%

“…Diacetone alcohol 15 gives only the low-frequency bonded peak (Av = 79 cm-1). When models are examined, a reason for this behavior is suggested.…”

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confidence: 99%

Hydrogen bonding. XIX. Intramolecular hydrogen bonding in aliphatic hydroxy ketones

Joris¹,

Schleyer²

1968

J. Am. Chem. Soc.

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The Aldol Condensation

Nielsen

Houlihan²

2011

Organic Reactions

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The aldol condensation takes its name from aldol (3‐hydroxybutanal) a name introduced by Wurtz who first prepared the beta‐hydroxy aldehyde from acetaldehdye in 1872. The aldol condensation includes reactions producing beta‐hydroxy aldehydes or beta‐hydroxy ketones by self condensations or mixed condensations of aldehydes and ketones as well as reactions leading to alpha, beta‐unsaturated aldehydes or alpha,beta‐unsaturated ketones formed by dehydration of intermediate beta‐aldols or beta‐ketals. The Claisen‐Schmidt condensation is most often taken to be the condensation of an aromatic aldehyde or ketone usually in the presence of a basic catalyst. The term aldol condensation has also been applied to many other condensations involving the reaction of an aldehyde or ketone. These condenations are discussed. The present review includes examples that are solely condensation reactions of aldehydes and ketones.

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Synthesen in der Isochinolin‐Reihe. I. Der strukturelle Verlauf einiger MICHAEL‐Additionen an 1‐Acetyl‐2‐arylalkyl‐3‐carbalkoxy‐4‐piperidone

Becker

1964

J. Prakt. Chem.

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Die MICHAEL‐Addition von Methylvinylketon und ähnlichen Verbindungen an 1‐Acetyl‐2‐arylalkyl‐3‐carbalkoxy‐4‐piperidione in Gegenwart von Triäthylamin liefert Derivate des 1‐Carbalkoxy‐2‐arylalkyl‐3‐aza‐6‐hydroxy‐bicyclo‐[3,3,1]‐nonanons‐(9). Diese Verbindungen zeichnen sich durch typische IR‐Spektren aus. Der Azabicyclo‐[3,3,1]‐nonanon‐Typ wird durch eine unabhängige Synthese bewiesen, sowie durch das UV‐ und IR‐Spektrum eines durch Dehydratisierung entstehenden ungesättigten Ketons, das nach der BREDT‐Regel nicht α,β‐ungesättigt sein kann, sondern vielmehr die typischen Homokonjugations‐Banden eines β,γ‐ungesättigten Ketons zeigt.Die Azabicyclo‐[3,3,1]‐nonanon‐Derivate lagern sich (mit zwei Ausnahmen) in Gegenwart von Natrium‐methylat glatt in 1‐Arylalkyl‐2‐acetyl‐6‐keto‐9‐carbalkoxy‐10‐hydroxydecahydroisochinoline um, die in konzentrierter Salzsäure leicht α,β‐ungesättigte Ketone liefern, was zugleich den Isochinolintyp beweist.Einige mit der Addition zusammenhängende stereochemische Fragen werden kurz diskutiert.

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Kondensationsreaktionen vom Aldoltypus V. Zur Konfiguration von Derivaten des 2,3-Cyclohexano-(1,3,3)-bicyclononan-2-ol-9-ons

Cited by 5 publications

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Hydrogen bonding. XIX. Intramolecular hydrogen bonding in aliphatic hydroxy ketones

Hydrogen bonding. XIX. Intramolecular hydrogen bonding in aliphatic hydroxy ketones

The Aldol Condensation

Synthesen in der Isochinolin‐Reihe. I. Der strukturelle Verlauf einiger MICHAEL‐Additionen an 1‐Acetyl‐2‐arylalkyl‐3‐carbalkoxy‐4‐piperidone

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