Premium
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
Abstract 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)