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Conformational preferences of α-fluoroketones may influence their reactivity
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Pattison, Graham (2017) Conformational preferences of α-fluoroketones may influence their reactivity. Beilstein Journal of Organic Chemistry, 13 . pp. 2915-2921. doi:10.3762/bjoc.13.284 ISSN 1860-5397.
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Official URL: http://dx.doi.org/10.3762/bjoc.13.284
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.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Other > Institute of Advanced Study | |||||||||
Library of Congress Subject Headings (LCSH): | Fluorine , Ketones | |||||||||
Journal or Publication Title: | Beilstein Journal of Organic Chemistry | |||||||||
Publisher: | Beilstein-Institut | |||||||||
ISSN: | 1860-5397 | |||||||||
Official Date: | 29 December 2017 | |||||||||
Dates: |
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Volume: | 13 | |||||||||
Page Range: | pp. 2915-2921 | |||||||||
DOI: | 10.3762/bjoc.13.284 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||
Date of first compliant deposit: | 4 January 2018 | |||||||||
Date of first compliant Open Access: | 4 January 2018 | |||||||||
RIOXX Funder/Project Grant: |
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