Activation energy calculation for the retro-ene elimination reaction of propylene from diallyl ether

Rodríguez, Leonardo Jiménez; Vidal, Alba B.; Izquierdo, Rodolfo; Fermín, José; Áñez, Rafael

doi:10.1016/j.theochem.2006.01.040

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Cited by 3 publications

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“…The most popular concerted mechanism for the retro-ene reaction includes a six-membered transition structure (TS). [1][2][3][4][5][6][7][8] Two convenient methods for direct conversion of sulfoxides to olens are base-catalyzed b-elimination and simple pyrolysis. A yield of 90% of propene was reported by heating of diisopropyl sulfoxide and potassium-tbutoxide in dimethyl sulfoxide as solvent for 17 hours at 358 K. 9 In comparison, thermal elimination requires a higher temperature but is potentially a cleaner reaction.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and mechanism of diallyl sulfoxide pyrolysis; a combined theoretical and experimental study in the gas phase

Izadyar

Gholami

2014

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Kinetics and mechanism of diallyl sulfoxide pyrolysis; a combined theoretical and experimental study in the gas phase

Izadyar

Gholami

2014

RSC Adv.

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Retro‐Ene Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The intramolecular thermolysis of organic compounds with an unsaturated functional group involving the transfer of a γ‐hydrogen to the unsaturated center via a six‐membered transition state to yield both ene and enophil is generally known as the retro ‐ene reaction or retro ‐ene fragmentation. The study finds that in most cases, this reaction involves a concerted mechanism, and gives a product with the stereochemical integrity preserved. This reaction does not take place among cyclic alkenes smaller than a seven‐membered ring or fused rings except for a cyclopropyl ring. This reaction has broad applications in organic synthesis.

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Characterization of covalent Ene adduct intermediates in “hydride equivalent” transfers in a dihydropyridine model for NADH reduction reactions

Libby

Mehl

2012

Bioorganic Chemistry

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Activation energy calculation for the retro-ene elimination reaction of propylene from diallyl ether

Cited by 3 publications

References 32 publications

Kinetics and mechanism of diallyl sulfoxide pyrolysis; a combined theoretical and experimental study in the gas phase

Kinetics and mechanism of diallyl sulfoxide pyrolysis; a combined theoretical and experimental study in the gas phase

Retro‐Ene Reaction

Characterization of covalent Ene adduct intermediates in “hydride equivalent” transfers in a dihydropyridine model for NADH reduction reactions

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