SN1ソルボリシスにおけるイオン対中間体の捕捉

石附 慎一郎; 森崎 めぐみ; 清水 宣次郎

doi:10.11494/kisoyuki.55.0.61.0

Abstracts of Symposium on Physical Organic Chemistry

55th Symposium on Organic Reactions

Session ID : P35

DOI https://doi.org/10.11494/kisoyuki.55.0.61.0

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Co-host: The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan (Cooperation)

selective trapping of intimate ion pair in SN1 solvolysis

*sin-ichiro ishidsuki, megumi morisaki, nobujiro shimizu

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Keywords: SN1 solvolysis, trapping of ion-pair, carbocation, selectivity

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Abstract

Product-forming steps in SN1 solvolysis of substituted benzyl-X substrate systems, where X is 2-R1-6-R2-substituted 4-methylphenolate (R1=C(CF3)2OH; R2=CH2OH, SiMe3, H), have been established in various solvents on the basis of selective trapping of intimate ion-pair intermediate by the nucleofuge X through ortho-substitution of the phenolate ion by the counter carbocation.

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