title: Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid.
abstract: The 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.
authors.affiliation: Instituto de Investigaciones Químicas, CSIC, Americo Vespucio 49, 41092 Seville, Spain.
authors.forename: Natalia
authors.initials: N
authors.lastname: Pérez-Hernández
authors.forename: Martín
authors.initials: M
authors.lastname: Febles
authors.forename: Cirilo
authors.initials: C
authors.lastname: Pérez
authors.forename: Ricardo
authors.initials: R
authors.lastname: Pérez
authors.forename: Matías L
authors.initials: ML
authors.lastname: Rodríguez
authors.forename: Concepción
authors.initials: C
authors.lastname: Foces-Foces
authors.forename: Julio D
authors.initials: JD
authors.lastname: Martín