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Cyclopentene oxide is used to prepare beta-amino alcohols by reacting with aromatic amines using bismuth trichloride as a catalyst.
Base-induced isomerization can give 2-cyclopentenol or cyclopentanone depending on the conditions. For discussion of the mechanism, see: J. Org. Chem., 61, 820 (1996), and references therein. Review of the rearrangement of epoxides to allylic alcohols: Org. React., 29, 345 (1983).
Wijma, H. J.; Floor, R. J.; Bjelic, S.; Marrink, S. J.; Baker, D.; Janssen, D. B. Enantioselective Enzymes by Computational Design and In Silico Screening. Angew. Chem. Int. Ed. 2015, 54 (12), 3726-3730.
Hua, Y. Z.; Yang, X. C.; Liu, M. M.; Song, X.; Wang, M. C.; Chang, J. B. Asymmetric Copolymerization of Cyclopentene Oxide and CO2 Using a Dinuclear Zinc-AzePhenol Catalyst: Enlightened by DFT Calculations. Macromolecules 2015, 48 (6), 1651-1657.
Gefahrenhinweise (EU): H225-H315-H319-H341-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. Suspected of causing genetic defects. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.