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- W2075836699 abstract "Enhanced rates of solvolysis have been reported for some isodrin derivatives, e.g. compounds 2, 3, 6 and 7 compared with anti-7-norbornene (1). The effect has been ascribed to the formation of laticyclic (2 + 2 + 0) π-delocalization on a carbocation such as 5. However, comparable rates of solvolysis were also observed for analogous monoenes 4, 8, 9 and 12, where no adequate explanation has been provided. Molecular modeling at both semiempirical and ab initio levels shows a good correlation between the stabilization energy of the cations and their kinetic data. The enhanced rate of solvolysis for 4, 8, 9 and 12 can be rationalized by strong effects of σ-bond participation in the transition state. For both series of compounds, the stabilization effect can be effectively transmitted either through space or through bonds. Copyright © 1998 John Wiley & Sons, Ltd." @default.
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- W2075836699 date "1998-12-01" @default.
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- W2075836699 title "Solvolysis of isodrin derivatives. Evidence of long-range ?-participation in the stabilization of carbocations" @default.
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- W2075836699 doi "https://doi.org/10.1002/(sici)1099-1395(199812)11:12<871::aid-poc76>3.0.co;2-o" @default.
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