Conformational preferences of α-fluoroketones may influence their reactivity

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)2915-2921
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume13
DOIs
Publication statusPublished - 29 Dec 2017

Keywords

  • Conformational analysis
  • Reactivity
  • Stereoelectronic effects
  • α-halogenated ketones

Fingerprint Dive into the research topics of 'Conformational preferences of α-fluoroketones may influence their reactivity'. Together they form a unique fingerprint.

  • Cite this