An anomalous effect of fluorine on the conformational equilibrium of 2-fluorocyclohexane-1,3-dione

TETRAHEDRON LETTERS

卷:60

Article

Andrade, Laize A. F.¹  Silla, Josue M.¹  Freitas, Matheus P.¹ 

[1] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras, MG, Brazil

关键词: Conformation analysis;    Organofluorine compounds;    Steric effect;    Dipolar interaction;    Hyperconjugation;   

DOI  :  10.1016/j.tetlet.2018.12.055

来源: Elsevier

【 摘 要 】

Conformational stabilities of 2-halocyclohexane-1,3-diones are strongly affected by steric and dipolar effects involving the carbonyl groups and the equatorial halogen. However, 2-fluorocyclohexane-1,3-dione has been found to be mostly equatorial, because of electron delocalization in this conformer that overcomes repulsive interactions, while the other halogen derivatives perform as expected. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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