A study of the aluminum hydride reduction of unsaturated cyclic epoxides

✍ Scribed by Eamonn F. Healy; J.D. Lewis; Amy B. Minniear

• Book ID: 104214675
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 134 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73457-5

✦ Synopsis

The aluminum hydride reduction of 3.4-cpoxycyclopentene to 3cyclopentenol has been previously observed' and the complete regiospekfkity of the reaction is confvmed h-. A mechanism is proposed involving initial complexation of the aMminum hydride anion with the Qbuble bond followed by hydride transfer to the 3-Carbon. Analysis of the atomic charges detumined fmm semiempirical electmstaic potentials support the proposed mechanism. Spectroscopic analysis of the resultant alcohol indicates the presence of an OH--rr intramolecular hydrogen bonded interaction.