π‐Strain‐Induced Electrophilicity in Small Cycloalkynes: A DFT Analysis of the Polar Cycloaddition of Cyclopentyne towards Enol Ethers | Zendy

Domingo Luis R. | Zendy; Pérez Patricia | Zendy; Contreras Renato | Zendy

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π‐Strain‐Induced Electrophilicity in Small Cycloalkynes: A DFT Analysis of the Polar Cycloaddition of Cyclopentyne towards Enol Ethers

Author(s) -

Domingo Luis R.,

Pérez Patricia,

Contreras Renato

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500466

Subject(s) - electrophile , chemistry , enol , cycloaddition , aryne , reactivity (psychology) , context (archaeology) , strain (injury) , computational chemistry , polar , electrophilic addition , density functional theory , substituent , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , paleontology , physics , alternative medicine , pathology , astronomy , biology

Small cycloalkynes possess a π‐strain‐induced electrophilicity related to the bending of the C sp 3–C sp –C sp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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