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Synthesis and Structure of Hydroxyl Acids of General Structure 7,7-Alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane- 1-carboxylic Acid

AuthorsPérez-Hernández, Natalia ; Febles, M. ; Pérez, Cirilo ; Pérez, Ricardo ; Rodríguez, Matias L.; Foces-Foces, Concepción ; Martín, Julio D.
Hydroxyl acids
Molecular structure
Hydrogen bonding
Carboxylic Acid
Issue Date10-Jan-2006
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 71(3): 1139-1151 (2006)
AbstractThe open-ended hollow tubular structure formed by inclusion of water molecules in the packing of the hydroxyl acid 1 (R1 = CH2OH, R2 = ethyl groups) led to the synthesis and structural study of their unsaturated analogues. In this article we report on a general and practical large-scale synthesis of hydroxyl acids that possess alkenyl and alkynyl appendages. Substitution of the ethyl groups in 1 with unsaturated two-carbon appendages has a different effect on the molecular structure and on the hydrogen-bonding pattern. No variation has been induced by substitution of only one ethyl group with a vinyl one, although the substitution of both ethyl groups with vinyl or acetylene appendages has the greatest effect on the molecular structure and results in different hydrogen-bonding motifs.
Description13 páginas, 4 figuras, 1 tabla, 11 esquemas.
Publisher version (URL)http://dx.doi.org/10.1021/jo052237p
Appears in Collections:(IQFR) Artículos
(IIQ) Artículos
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