Unexpected halogen exchange with halogenated solvents in the iron(III) promoted oxa-alkyne and aza-alkyne Prins cyclizations
An unexpected halide exchange with halogenated solvents using iron(III) halides as promoters in oxa- and aza-alkyne Prins cyclizations have been observed. The process is specific for alkynes, while during the Prins cyclization using both homoallylic alcohols and N-tosyl amines, the halide participation from the halogenated solvent was absent. Calculation at ab initio level provides substantiation of the proposed model.
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Main Authors: | , , , , |
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Other Authors: | |
Format: | artículo biblioteca |
Language: | English |
Published: |
University of Michigan
2006-11-29
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Subjects: | Prins cyclization, Aza-Prins cyclization, Fe(III) halides, Vinyl cations, Halogen abstraction, |
Online Access: | http://hdl.handle.net/10261/212248 |
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Summary: | An unexpected halide exchange with halogenated solvents using iron(III) halides as promoters in
oxa- and aza-alkyne Prins cyclizations have been observed. The process is specific for alkynes,
while during the Prins cyclization using both homoallylic alcohols and N-tosyl amines, the halide
participation from the halogenated solvent was absent. Calculation at ab initio level provides
substantiation of the proposed model. |
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