Kinetics of the base-induced conversion of 2-pyrazolines to cyclopropanes

Jones, W. M.; Sanderfer, Paul O.; Baarda, D. G.

doi:10.1021/jo01280a019

Cited by 4 publications

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“…[31][32][33] The stability of such products is highly dependent on the alkene used. It is known that decomposition can be spontaneous or promoted by acids or bases [34] with dinitrogen loss, and this leads to the corresponding cyclopropyl derivatives (Scheme 2). Stable 4,5-dihydro-1H-pyrazoles are prepared by acid catalysis with a,b-unsaturated aldehydes and ethyl diazoacetate [35] or with metal Lewis acids with other electron-deficient alkenes.…”

Section: Resultsmentioning

confidence: 99%

Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

et al. 2014

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Diazoacetate esters proved to be suitable neutral guests for\ud the self-assembled resorcin[4]arene hexameric capsule. The hydrogen- bonded supramolecular host catalyzed the 1,3-dipolar cycloaddition reaction between diazoacetate esters and electron- poor alkenes such as acrolein, acrylonitrile, crotonaldehyde, trans-2-hexenal, methyl, and butyl acrylate,\ud which led to the corresponding 4,5-dihydro-1H-pyrazole\ud derivatives. The cycloaddition reaction occurred within the\ud cavity of the capsule. In fact, substantial inhibition of the catalytic activity was observed by employing tetraethylammonium tetrafluoroborate characterized by greater affinity for the hexameric capsule as a competitive guest; its presence inhibited access of the substrates. The 1,3-dipolar cycloaddition reaction between diazoacetate esters and acrylate esters of different lengths showed a significant degree of substrate selectivity owing to the encapsulation of the reagents before the cycloaddition reaction

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Section: Resultsmentioning

confidence: 99%

Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

et al. 2014

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Conformation changes induced in 2‐spiro‐substituted cephalosporin sulphoxides by the configuration of the spiro bond: A combined ¹H and ¹³C NMR study

Erdödiné-Kövér¹,

Jaszberenyi

1984

Org. Magn. Reson.

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Studies in terpenoids — VIII (1): Some observations on (−)-3, 3a, 4, 5, 6, 7-hexahydro-3, 3, 6-trimethyl-2H-indazole and its conversion to (+)--carane

Ramamoorthy

Rao

1967

Tetrahedron Letters

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Kinetics of the base-induced conversion of 2-pyrazolines to cyclopropanes

Cited by 4 publications

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Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

Conformation changes induced in 2‐spiro‐substituted cephalosporin sulphoxides by the configuration of the spiro bond: A combined ¹H and ¹³C NMR study

Studies in terpenoids — VIII (1): Some observations on (−)-3, 3a, 4, 5, 6, 7-hexahydro-3, 3, 6-trimethyl-2H-indazole and its conversion to (+)--carane

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Kinetics of the base-induced conversion of 2-pyrazolines to cyclopropanes

Cited by 4 publications

References 0 publications

Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

Supramolecular Encapsulation of Neutral Diazoacetate Esters and Catalyzed 1,3‐Dipolar Cycloaddition Reaction by a Self‐Assembled Hexameric Capsule

Conformation changes induced in 2‐spiro‐substituted cephalosporin sulphoxides by the configuration of the spiro bond: A combined 1H and 13C NMR study

Studies in terpenoids — VIII (1): Some observations on (−)-3, 3a, 4, 5, 6, 7-hexahydro-3, 3, 6-trimethyl-2H-indazole and its conversion to (+)--carane

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Conformation changes induced in 2‐spiro‐substituted cephalosporin sulphoxides by the configuration of the spiro bond: A combined ¹H and ¹³C NMR study