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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GP BJOC conformational preferences of alpha-fluoroketones.docx - Whole Document Available under License Creative Commons Attribution 4.0 International. 693kB |
Item Type: | Article |
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Item Status: | Live Archive |
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 |
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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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