Reactivity of chlorotrifluoromethylcarbene: activation parameters for halocarbene-alkene addition reactions
Robert A Moss1, Lei Wang, Karsten Krogh-Jespersen
1Department of Chemistry and Chemical Biology, Rutgers University, The State University of New Jersey , New Brunswick, New Jersey 08903, United States.
Abstract:
Activation parameters are reported for ClCCF3 additions to three alkenes (tetramethylethylene, cyclohexene, and 1-hexene). The results are compared to those for CCl2, CClF, and CF2. Activation enthalpies decrease as the carbene stability decreases and its electrophilicity increases, and also as alkene reactivity (degree of alkylation) increases. Activation entropies decrease in parallel with activation enthalpies, suggesting the operation of enthalpy-entropy compensation in these carbene additions.
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