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- W1976057143 abstract "The semi-π analogue of double hyperconjugation (“hyperconjugation/conjugation”) has been examined in 4-isopropylidenecyclohexyl mesylate (4-OMs) by comparison with the saturated analogue, trans-4-isopropylcyclohexyl mesylate (5-OMs). The unsaturated substrate reacts in 97% trifluoroethanol only four times faster than the saturated substrate. Raber−Harris plots indicate that both substrates react by ks mechanisms; i.e., solvolysis occurs with solvent assistance rather than carbocation formation. These results are consistent with the absence of a direct, through-bond interaction of the double bond with the reactive center. The absence is caused at least in part by less than ideal overlap of the γ,δ π orbitals with the α,β σ orbitals. In contrast, an electron-rich tin atom attached to the 4-position provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation." @default.
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- W1976057143 date "1996-01-01" @default.
- W1976057143 modified "2023-10-16" @default.
- W1976057143 title "The Interaction of π Orbitals with a Carbocation over Three σ Bonds" @default.
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- W1976057143 doi "https://doi.org/10.1021/jo951643d" @default.
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