Zur Kenntnis des Kohlenstoffringes. 48. Mitteilung. Über den Einfluss der Grösse des vielgliedrigen Ringes auf die Eigenschaften der 2,6‐Polymethylen‐4‐nitro‐phenole

Prelog, V.; Wiesner, K.; Ingold, W.; Häfliger, O.

doi:10.1002/hlca.19480310518

Cited by 30 publications

References 11 publications

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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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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Unusual Reactions of Halo[5]metacyclophanes

Wijsman¹,

Boesveld²,

Goedheijt³

et al. 2002

Eur. J. Org. Chem.

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The synthesis of novel [5]metacyclophanes 1 has been achieved either by an improved version of the general approach starting from halobicyclo[5.3.0]dec-1(7)-enes 2 or by nucleophilic substitution of 11-chloro[5]metacyclophanes. Conformational analysis of 1 revealed that the exo conformation, in which the pentamethylene bridge is pointing away from the aromatic ring, is strongly preferred both for very small and for very large substituents at the aromatic interbridge position 11, whereas medium-sized substituents induce the occurrence of minor amounts of the endo conformer. In Diels−Alder reactions with dienophiles, compounds 1 behaved like reactive dienes, adding at positions 8 and 11 of the aromatic ring. Substitution by chlorine, though, reduced the reaction rate; the unsymmetrical dienophile acrylonitrile showed little preference for the two possible regioisomeric adducts 8 and 9. Similarly, compounds 1 were unusually reactive towards acid, and interesting and unforeseen rearrangements were observed. Depending on the substituent at position 11, acid treatment of 1 afforded either ortho-annu-

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Zur Kenntnis des Kohlenstoffringes. 48. Mitteilung. Über den Einfluss der Grösse des vielgliedrigen Ringes auf die Eigenschaften der 2,6‐Polymethylen‐4‐nitro‐phenole

Cited by 30 publications

References 11 publications

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

The Aldol Condensation

Unusual Reactions of Halo[5]metacyclophanes

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