Intramolecular Hydrogen Bonding in α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-epoxycyclopentanol Diastereomers

Intramolecular Hydrogen Bonding in α-Epoxy Alcohols: A Conformational Analysis of 1,2-Dialkyl-2,3-epoxycyclopentanol Diastereomers

Geometry optimizations for 11 1,2-disubstituted-2,3-epoxycyclopentanol diastereomers were studied using the M06-2X/cc-pVTZ method and basis set to probe mechanistic details in the α-epoxy alcohol semipinacol rearrangement reaction. Electronic energies of active cis diastereomers are on average 0.9 k...

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Veröffentlicht in:Chemistry letters 2018-02, Vol.47 (2), p.156-159
Hauptverfasser: Abdo, Yasmeen A., Weeks, Justin W., Layfield, William, Tremlett, William M., Graham, Joshua W., Tabor, Mikayla E., Causey, Sarah E., Carr, Jeremy M., Tschumper, Gregory S.
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Sprache:eng
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Zusammenfassung:Geometry optimizations for 11 1,2-disubstituted-2,3-epoxycyclopentanol diastereomers were studied using the M06-2X/cc-pVTZ method and basis set to probe mechanistic details in the α-epoxy alcohol semipinacol rearrangement reaction. Electronic energies of active cis diastereomers are on average 0.9 kcal mol−1 lower than trans diastereomers. Intramolecular hydrogen bonding stabilizes the cis substrate energy by 3.4 kcal mol−1, on average.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.170932