Unexpected halogen exchange with halogenated solvents in the iron(III) promoted oxa-alkyne and aza-alkyne Prins cyclizations

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Abstract

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. ©ARKAT USA, Inc.

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Miranda, P. O., Carballo, R. M., Ramírez, M. A., Martín, V. S., & Padrón, J. I. (2007). Unexpected halogen exchange with halogenated solvents in the iron(III) promoted oxa-alkyne and aza-alkyne Prins cyclizations. Arkivoc, 2007(4), 331–343. https://doi.org/10.3998/ark.5550190.0008.430

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