Conformational preferences of α-fluoroketones may influence their reactivity.

Pattison, Graham (2017) Conformational preferences of α-fluoroketones may influence their reactivity. Beilstein J. Org. Chem., 13 . pp. 2915-2921. ISSN 1860-5397

Full content URL: https://doi.org/10.3762/bjoc.13.284

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Conformational preferences of α-fluoroketones may influence their reactivity.
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Abstract

Fluorine has been shown in many cases to impart specific and predictable effects on molecular conformation. Here it is shown that these conformational effects may have an influence on reactivity through studying the relative reactivity of various α-halogenated ketones towards borohydride reduction. These results demonstrate that the α-fluoro ketones are in fact a little less reactive than the corresponding α-chloro and α-bromo derivatives. It is suggested, supported by computation, that this effect is due to reactive conformations in which the C–X bond is orthogonal to the carbonyl group for good orbital overlap being disfavoured in the case of fluoro ketones.

Keywords:fluorination, Molecular Conformation, reactivity, ketone
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:52243
Deposited On:31 Oct 2022 14:39

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