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Title

Fe(III) Halides as Effective Catalysts in Carbon−Carbon Bond Formation:  Synthesis of 1,5-Dihalo-1,4-dienes, α,β-Unsaturated Ketones, and Cyclic Ethers

AuthorsMiranda, Pedro O. ; Díaz Díaz, David ; Padrón, Juan I. ; Ramírez, Miguel A.; Martín, Víctor S.
KeywordsHydrocarbons
Aldehydes
Inorganic compounds
Ketones
Halogens
Issue Date23-Nov-2004
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 70(1): 57–62 (2004)
AbstractIron(III) halides have proven to be excellent catalysts in the coupling of acetylenes and aldehydes. When terminal acetylenes were used the main products obtained were 1,5-dihalo-1,4-dienes with (E,Z)-stereochemistry contaminated in some cases with (E)-α,β-unsaturated ketones. The former carbonyl derivatives were the sole products isolated when nonterminal aromatic alkynes were used. When homopropargylic alcohols were used, a Prins-type cyclization occurred yielding 2-alkyl-4-halo-5,6-dihydro-2H-pyrans. In addition, anhydrous ferric halides are also shown to be excellent catalysts for the standard Prins cyclization with homoallylic alcohols. Isolation of an intermediate acetal, calculations, and alkyne hydration studies provide substantiation of a proposed mechanism.
Publisher version (URL)https://doi.org/10.1021/jo048410j
URIhttp://hdl.handle.net/10261/212284
DOI10.1021/jo048410j
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(IPNA) Artículos
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