Unexpectedly Facile Solvolysis of 3-Oxobicyclooct-1-yl Triflates: Through-Bond Interaction of the β-Carbonyl Lone Pair with the Cationic p Orbital

DOI: 10.1021/jo00277a006

Source and publish data:

Journal of Organic Chemistry p. 3772 - 3773 (1989)

Update date:2022-08-25

Topics:

Authors:

Takeuchi, Ken'ichi

Yoshida, Masayasu

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Article abstract of DOI:10.1021/jo00277a006

The title compounds solvolyze in 80percent ethanol at 25 deg C 10³-10⁴ times faster than predicted from the inductive effect of the carbonyl group, providing the first example of the through-bond interaction of the β-carbonyl lone pair with the cationic p orbital.

Full text of DOI:10.1021/jo00277a006

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