SOLVOLYTIC REACTIVITY OF 1-(1-METHYL-2-PYRROLYL)-2,2,2-TRIFLUOROETHYL p-NITROBENZOATE

DOI: 10.1016/S0040-4039(00)99454-1

Source and publish data:

Tetrahedron Letters p. 1319 - 1322 (1989)

Update date:2022-08-02

Topics:

Authors:

Kwong-Chip, Jean-Marc

Tidwell, Thomas T.

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Article abstract of DOI:10.1016/S0040-4039(00)99454-1

1-(1-Methyl-2-pyrrolyl)-2,2,2-trifluoroethyl p-nitrobenzoate (1) solvolyses to form a carbocation intermediate 4 as evidenced by the dependence on the solvent ionizing power Y_OTs and the formation of substitution products.The rate ratio k(H)/k(CF₃) of only 40 indicates strong electron donation to the destabilized carbocation.

Full text of DOI:10.1016/S0040-4039(00)99454-1

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