Composés alicycliques à carbone quaternaire IV. Phénomène de conjugaison chez les 1‐éthoxycarbonyl‐cyclopropane‐spiro‐cyclanes

Chiurdoglu, Grégoire; Laune, J M; Poelmans, M.

doi:10.1002/bscb.19560650305

Cited by 16 publications

(1 citation statement)

References 10 publications

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“…Nitrone 29 was synthesized starting from the known ester 26 34 in an analogous manner. Neither nitrone 25a, b , nor 29 showed any tendency to undergo the intramolecular cycloaddition and remained intact even at elevated temperatures (∼60-70 °C).…”

Section: Resultsmentioning

confidence: 99%

Cyclopentadienones via a Tandem C‐Cyclopropylnitrone Cyclization‐Cycloreversion Sequence

Erden

Gärtner

et al. 2017

Eur J Org Chem

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Aldonitrones derived from spiro[2.4]hepta-4,6-diene-1-carbaldehyde and its benzo analog undergo a tandem uncatalyzed intramolecular cyclopropane-nitrone cyclization-5,6-dihydro-1,2-oxazine cycloreversion to give cyclopentadienones. Similarly, the NH-nitrone generated in situ from spiro[cyclopropane-1,1′-indene]carbaldehyde oxime leads to benzocyclopentadienone (1H-inden-1-one) by the same mechanism. DFT calculations are in favor of a concerted yet highly asynchronous pathway for the cyclizations. Control experiments with the dihydro and tetrahydro derivatives show that the spirocyclopentadiene unit is essential for the success of the reaction, invoking spiroconjugative effects for increased cyclopropane reactivity.

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Section: Resultsmentioning

confidence: 99%

Cyclopentadienones via a Tandem C‐Cyclopropylnitrone Cyclization‐Cycloreversion Sequence

Erden

Gärtner

et al. 2017

Eur J Org Chem

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The Reactions of Diazoacetic Esters with Alkenes, Alkynes, Heterocyclic and Aromatic Compounds

Dave

Warnhoff

2011

Organic Reactions

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After the first unsuccessful attempt of Curtius in 1884 to affect the reaction of ethyl diazoacetate with toluene other researchers studied the reaction. Later, Buchner and Curtius treated several aromatic, olefinic, and acetylenic compounds with diazoacetic esters to form cyclopropanes. Since then the reactions of diazoacetates with various unsaturated compounds have been studied. The carbalkoxy carbenes are of interest since they are believed to be intermediates in higher temperature thermal and photochemical reactions of diazoacetates.

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Composés alicycliques à carbone quaternaire V. Synthèse et spectres infra‐rouges de quelques 2‐éthoxycarbonyl‐1‐oxacyclopropane‐spiro‐cyclanes

Chiurdoglu

Mathieu

Baudet

et al. 1956

Bulletin des Soc Chimique

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RESUMELes 2-Cthoxycarbonyl-l-oxacyclopropane-spiro-cyclobutane (I), -cyclopentane (11), -cyclohexane (IV), les dCrivCs 2 , 4 , 5, 6, -mCthyles (V a VIII) de ce dernier e t le 2-mCthyl-2-kthoxycarbonyl-l-oxacyc~opropane-spirocyclopentane (111) sont dCcrits par I'intermCdiaire de leurs constantes et de leurs spectres infra-rouges et, pour certains, Raman.Le fait essentiel, rCvC1C par les spectres est l'existence, chez ces esters glyeidiques, d'un net dCdoublement de la bande carbonyle : 1730 cm-I et 1750 cm-I. Ce dkdoublement s'observe, en outre, chez le 2-mkthyl-2-Cthoxycarbonyl-1 -oxacyclopropane (X) et pas chez le 2-Ctlioxycarbonyl-1-oxacyclopropane (IX) ou encore chez le 'L-carbo-carboxy-l-oxacyclopropane-spirocyclohexane (XI) et pas chez le sel de sodium correspondant.

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Composés alicycliques à carbone quaternaire IV. Phénomène de conjugaison chez les 1‐éthoxycarbonyl‐cyclopropane‐spiro‐cyclanes

Cited by 16 publications

References 10 publications

Cyclopentadienones via a Tandem C‐Cyclopropylnitrone Cyclization‐Cycloreversion Sequence

Cyclopentadienones via a Tandem C‐Cyclopropylnitrone Cyclization‐Cycloreversion Sequence

The Reactions of Diazoacetic Esters with Alkenes, Alkynes, Heterocyclic and Aromatic Compounds

Composés alicycliques à carbone quaternaire V. Synthèse et spectres infra‐rouges de quelques 2‐éthoxycarbonyl‐1‐oxacyclopropane‐spiro‐cyclanes

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