Rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions
Heterogeneous polymer-supported triphenylphosphine oxides based on the rasta resin architecture have been synthesized, and applied as reagent precursors in a wide range of halogenation reactions. The rasta resin-triphenylphosphine oxides were reacted with either oxalyl chloride or oxalyl bromide to form the corresponding halophosphonium salts, and these in turn were reacted with alcohols, aldehydes, aziridines and epoxides to form halogenated products in high yields after simple purification. The polymersupported triphenylphosphine oxides formed as a byproduct during these reactions could be recovered and reused numerous times with no appreciable decrease in reactivity.
Xia, Xuanshu,Toy, Patrick H.
supporting information
p. 1397 - 1405
(2014/07/22)
Microwave-assisted benzyl mono- and dibromination in diethyl carbonate as environmentally friendly alternative to radical bromination in carbon tetrachloride
An environmentally friendly benzyl mono- and di-bromination synthetic procedure was developed that is superior to the classic carbon tetrachloride bromination procedure in both reaction time and isolated yield. This new reaction was performed in diethyl carbonate as reaction media using microwave instead of conventional heating. Both the solvent and the brominating reagent N-bromosuccinimide (prepared from succinimide obtained from the reaction mixture) are recyclable. Practically, the preparation of our target compounds was completed in less than two hours. The Royal Society of Chemistry.
Pingali, Subramanya R. K.,Upadhyay, Sunil K.,Jursic, Branko S
experimental part
p. 928 - 933
(2011/05/15)
THE REACTION OF ETHANEDIYL S,S-ACETALS WITH HALOGENES
Cyclic thioacetals and thioketals (1,3-dithiolanes) are reported to react smoothly with halogens in a 1:1 molar ratio, at room temperature in anhydrous carbon tetrachloride.The mechanistic aspects of the reaction are considered and evidence is shown of the itermediacy of monocationic rather than the previously postulated dicatonic species in the cleavage reactions of 1,3-dithiolanes of aromatic ketones.
Caputo, Romualdo,Ferreri, Carla,Palumbo, Giovanni,Capozzi, Giuseppe
p. 2369 - 2376
(2007/10/02)
Reactions of Carbonyl Compounds with Tervalent Phosphorus Reagents. Part 12. Aromatic Aldehydes with Bromophosphines and Phosphorus Tri-iodide
The reactions of aromatic aldehydes with phosphorus tribromide (4a), with phosphorus tri-iodide (3), and with bromodiphenylphosphine (4b) have been investigated in detail.Both the trihalides react as electrophiles to produce high yields of the appropriate benzylidene dihalide.Thereafter, these reactions differ from each other and from that of phosphorus trichloride.Bromodiphenylphosphine (4b) reacts in biphilic fashion to produce (α-bromobenzyl)diphenylphosphine oxide (15).This oxide is readily dehalogenated under the reaction conditions and in model studies.Cyanodiphenylphosphine is unreactive towards benzaldehyde.These halogenophosphine reactions confirm the generality of the trends first observed with chlorophosphines and that the nature of the other two ligands on phosphorus determines the mode of reaction with aldehydes.
Michie, Jacqui,Miller, J. Allen,Nunn, M. John,Stewart, Denis
p. 1744 - 1749
(2007/10/02)
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