10.1021/jo052237p.s001 Natalia Pérez-Hernández Natalia Pérez-Hernández Martín Febles Martín Febles Cirilo Pérez Cirilo Pérez Ricardo Pérez Ricardo Pérez Matías L. Rodríguez Matías L. Rodríguez Concepción Foces-Foces Concepción Foces-Foces Julio D. Martín Julio D. Martín Synthesis and Structure of Hydroxyl Acids of General Structure 7,7-Alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane- 1-carboxylic Acid American Chemical Society 2006 appendages hydroxyl acid 1 CH 2 OH substitution ethyl groups synthesis 2006-02-03 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Synthesis_and_Structure_of_Hydroxyl_Acids_of_General_Structure_7_7_Alkenyl_alkynyl_5_hydroxymethyl_6_oxabicyclo_3_2_1_octane_1_carboxylic_Acid/3240004 The open-ended hollow tubular structure formed by inclusion of water molecules in the packing of the hydroxyl acid <b>1</b> (R<sub>1</sub> = CH<sub>2</sub>OH, R<sub>2</sub> = 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 <b>1</b> 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.