78102-56-4Relevant academic research and scientific papers
Halogen Epoxides, 5. Mixed Halogenated 2,3-Dihalo-2,3-diethyloxiranes: Synthesis, Limits of Existence, and Reactions with AgBF4
Spraul, Manfred,Griesbaum, Karl
, p. 2641 - 2652 (2007/10/02)
3-Chloroperbenzoic acid reacts with mixed 3,4-dihalo-3-hexenes (1) to give the corresponding 2,3-dihalooxiranes having F/Cl (2a)-, F/Br (2b)-, F/I (2c)-, and Cl/Br (2d)-substituents, however, not that having Cl/I (2e)-substituents.In 1:1-reactions with AgBF4, the epoxides 2a - d were selectively attacked at the respective higher halogen homologue by silver ions.The fluorinated epoxides 2a - c afforded high yields of 4,4-difluoro-3-hexanone (12a), while the Cl/Br-epoxide 2d provided 4-chloro-4-fluoro-3-hexanone (12d) as the major product.
Halogen Epoxides, 3. Reactions of 2-Chloro- and 2,3-Dichlorooxiranes with Silver Tetrafluoroborate: Synthesis of α-Fluorinated Carbonyl Compounds
Griesbaum, Karl,Keul, Helmut,Kibar, Riza,Pfeffer, Bernd,Spraul, Manfred
, p. 1858 - 1870 (2007/10/02)
Reactions of chlorinated oxiranes with silver tetrafluoroborate in ether have been investigated.Substituted-2-chlorooxiranes (4a - e) afforded the corresponding α-fluorocarbonyl compounds (7a - e) as major products and the isomeric α-chlorocarbonyl compounds (8a - e) as minor products.Substituted 2,3-dichlorooxiranes (10, 14, 20, 24) yielded the isomeric α,α-dichloroketones (13, 19, 22, 26b, 29b) as well as the corresponding α-chloro-α-fluoroketones (12, 17, 21, 26a, 29a) and α,β-unsaturated α-chloroketones (18, 23, 27, 30).The course of the reaction was rationalized.Similar reaction with α-chloroketones and with α,α-dichloroketones succeeded only at substrates (8b, 35) in which the chlorine substituents were in benzylic positions.
