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Activation Parameters for Additions to Alkenes of Arylchlorocarbenes with Enhanced Electrophilicity

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journal contribution
posted on 07.08.2015, 00:00 by Lei Wang, Karsten Krogh-Jespersen, Robert A. Moss
Activation parameters are reported for additions of phenylchlorocarbene (PhCCl), pentafluorophenylchlorocarbene (F5-PhCCl), and 3,5-dinitrophenyl-chlorocarbene (3,5-DN-PhCCl) to tetramethylethylene (TME), cyclohexene, and 1-hexene. The order of activation enthalpies is F5-PhCCl > PhCCl > 3,5-DN-PhCCl. Activation enthalpies also increase as the degree of alkene alkylation decreases. In general, the entropies of activation increase in tandem with the enthalpies of activation.