Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 14, Pages 2956-2963Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301779
Keywords
Kinetics; Linear free energy relationships; Electrophilicity; Cycloaddition; Ylides; Alkenes
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 749]
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The kinetics of the reactions of maleic anhydride, N-methylmaleimide, fumaronitrile, diethyl fumarate, and diethyl maleate with pyridinium and sulfonium ylides were studied in DMSO at 20 degrees C. All of the reactions were found to follow a second-order rate law, and can be described by the linear free energy relationship logk(2) (20 degrees C) = s(N)(N + E), where N and s(N) are solvent-dependent nucleophile-specific parameters, and E is an electrophile-specific parameter. The electrophilicity parameters E of the investigated acceptor-substituted alkenes were derived from the linear correlations of (logk(2))/s(N) vs. N, and range from -19.8 to -11.1.
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