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Pérez-Hernández N, Febles M, Pérez C, et al. Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid. J Org Chem. 2006;71(3):1139-51doi: 10.1021/jo052237p.
Pérez-Hernández, N., Febles, M., Pérez, C., Pérez, R., Rodríguez, M. L., Foces-Foces, C., & Martín, J. D. (2006). Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid. The Journal of organic chemistry, 71(3), 1139-51. https://doi.org/10.1021/jo052237p
Pérez-Hernández, Natalia, et al. "Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid." The Journal of organic chemistry vol. 71,3 (2006): 1139-51. doi: https://doi.org/10.1021/jo052237p
Pérez-Hernández N, Febles M, Pérez C, Pérez R, Rodríguez ML, Foces-Foces C, Martín JD. Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid. J Org Chem. 2006 Feb 03;71(3):1139-51. doi: 10.1021/jo052237p. PMID: 16438532.
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J Org Chem. 2006 Feb 03;71(3):1139-51. doi: 10.1021/jo052237p.

Synthesis and structure of hydroxyl acids of general structure 7,7-alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid.

The Journal of organic chemistry

Natalia Pérez-Hernández, Martín Febles, Cirilo Pérez, Ricardo Pérez, Matías L Rodríguez, Concepción Foces-Foces, Julio D Martín

Affiliations

  1. Instituto de Investigaciones Químicas, CSIC, Americo Vespucio 49, 41092 Seville, Spain.

PMID: 16438532 DOI: 10.1021/jo052237p

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.

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