Title

Neighboring group participation by the pyrrole nucleus

Document Type

Article

Publication Date

1-1-1981

Abstract

Using proton and carbon-13 NMR spectroscopy, the transformation of 2-hydroxyethylpyrroles (5,15) into 2-haloethylpyrroles by treatment with thionyl chloride or carbon tetrabromide/triphenylphosphine is shown to proceed by randomization of the two side-chain carbon atoms. A spirocyclopropylpyrrolium ion (19) is postulated as an intermediate in this unexpected process. © 1981.

Publication Source (Journal or Book title)

Tetrahedron Letters

First Page

1291

Last Page

1294

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