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Title

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

AuthorsMiranda, Pedro O. ; Carballo, Rubén M.; Ramírez, Miguel A.; Martín, Víctor S.; Padrón, Juan I.
KeywordsPrins cyclization
Aza-Prins cyclization
Fe(III) halides
Vinyl cations
Halogen abstraction
Issue Date29-Nov-2006
PublisherUniversity of Michigan
CitationArkivoc: Online Journal Organic Chemistry (4): 331-343 (2007)
AbstractAn 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.
Publisher version (URL)http://dx.doi.org/10.3998/ark.5550190.0008.430
URIhttp://hdl.handle.net/10261/212248
DOI10.3998/ark.5550190.0008.430
ISSN1551-7012
E-ISSN1551-7004
Appears in Collections:(IPNA) Artículos
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