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.

Saved in:
Bibliographic Details
Main Authors: Miranda, Pedro O., Carballo, Rubén M., Ramírez, Miguel A., Martín, Víctor S., Padrón, Juan I.
Other Authors: Ministerio de Educación y Ciencia (España)
Format: artículo biblioteca
Language:English
Published: University of Michigan 2006-11-29
Subjects:Prins cyclization, Aza-Prins cyclization, Fe(III) halides, Vinyl cations, Halogen abstraction,
Online Access:http://hdl.handle.net/10261/212248
Tags: Add Tag
No Tags, Be the first to tag this record!