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• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 70-11-1 α-bromoacetophenone 
• 28483-60-5 Acetonyltributylstananne 
• 14583-98-3 1-tributylstannanyl-propan-2-one 

Relevant academic research and scientific papers

Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group

We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, α-bromoketones, α-bromoesters, and α-bromoamides were applied to this system to produce the coupling compounds.

Catalytic Effect of Five-Coordinate Organotin Bromide or Tetraphenylstibonium Bromide on the Chemo- and Stereoselective Addition of Tin Enolate to α-Halo Ketone

Two types of catalysts, five-coordinate organotin bromides and tetraphenylstibonium bromide, similarly promoted the selective addition of tin enolates to the carbonyl moiety in α-halo ketones.The reaction with 2-chlorocyclohexanones and the enolates gave

NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward α-Halo Ketone or α-Halo Imine

NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the 119Sn NMR spectrum and increased coupling constants J(119Sn-13C), compared wit

Facile Control of Regioselectivity in the Reaction of Tin Enolates with α-Halogeno Carbonyls by Additives

Tin enolates 1 reacted with α-halogeno ketones 2 and esters 10 to give a variety of 1,4-diketones 3 and γ-keto esters 11, respectively, in the presence of appropriate additives such as hexamethylphosphoric triamide (HMPT), tributylphosphine oxide and tetrabutylammonium bromide, while complexation of these additives with tributyltin bromide allowed catalytic production of β-keto oxiranes 4 instead of 3.The reaction mechanism for the preparation of 1,4-diketone 3 is discussed.

CHANGE OF REGIOSELECTIVITY IN THE REACTION OF TIN ENOLATES AND α-BROMO KETONES; SYNTHESIS OF 1,4-DIKETONES UNDER NON-RADICAL CONDITIONS

The reaction of tin enolates with α-halogeno ketones, strikingly effected by the addition of phosphine oxides to the reaction mixture, produced 1,4-diketones under mild conditions; the addition was shown to proceed in a non-radical manner.

Synthesis of Substituted Cyclic Ethers from Halo Ketones and Halo Aldehydes by Palladium-Catalyzed Coupling with Organotin Reagents

The palladium-catalyzed reaction of a variety of halo ketones or halo aldehydes with acetonyl- and allyltin reagents gives cyclic ethers in good yields.Oxiranes, oxetanes, and tetrahydrofurans can be obtained under mild reaction conditions.The use of palladium catalyst containing chiral monophosphine ligands gave a small enantiomeric excess (up to 19percent) of a chiral oxirane from an α-halo ketone.The allyl- and acetonyloxirane products tend to undergo further transformations in prolonged reactions: allyloxiranes rearrange to α-allyl aldehydes and acetonyloxiranes dehydrate to give substituted furans.The mechanism of the reaction appears to involve addition of the organotin ligand to the carbonyl, followed by palladium(II)-catalyzed cyclization of the tin alkoxides.