Tetrahedron Letters p. 6647 - 6648 (1994)
Update date:2022-08-23
Topics:
Healy, Eamonn F.
Lewis
Minniear, Amy B.
The aluminum hydride reduction of 3,4-epoxycyclopentene to 3-cyclopentenol has been previously observed1 and the complete regiospecificity of the reaction is confirmed here. A mechanism is proposed involving initial complexation of the aluminum hydride anion with the double bond followed by hydride transfer to the 3-Carbon. Analysis of the atomic charges determined from semiempirical electrostaic potentials support the proposed mechanism. Spectroscopic analysis of the resultant alcohol indicates the presence of an O-H''''''π intramolecular hydrogen bonded interaction.
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