32831-01-9Relevant articles and documents
Visible Light-Promoted Friedel-Crafts-Type Chloroacylation of Alkenes to β-Chloroketones
Patil, Dilip V.,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 3018 - 3022 (2020/04/09)
The photoredox chloroacylation of alkenes has been developed as a substitute for the Friedel-Crafts acylation of alkenes to β-chloroketones. The direct generation of acyl radical species from acid chlorides under the photoredox conditions allows the formation of β-chloroketones without dehydrochlorination with the help of KHCO3. The synthetic utility of the current method is demonstrated in the one-pot synthesis of dihydroisoxazole, dihydropyrazole, and dihydropyrimidine-2-thione in 1 mmol scale.
Desulfurative Chlorination of Alkyl Phenyl Sulfides
Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
, p. 918 - 921 (2017/02/26)
The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.
AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives
Miyahara, Yuji,Ito, Yoshio N.
, p. 6801 - 6807 (2014/08/18)
Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.
Trifluoroacetic anhydride - Catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones
Roscales, Silvia,Rincón, ángela,Buxaderas, Eduardo,Csák?, Aurelio G.
experimental part, p. 4721 - 4724 (2012/09/08)
The conjugate addition of boronic acids to α,β-unsaturated ketones catalyzed by acylating reagents has been explored. The results show that trifluoroacetic anhydride catalyzes the addition of vinylboronic acids under experimentally simple and metal-free conditions for a variety of substrates with good yields.
TELLURIUM TETRACHLORIDE AS A MILD DEPROTECTION REAGENT FOR ACETALS AND THIOACETALS
Tani, Hiroyuki,Inamasu, Tokuo,Masumoto, Kazunori,Tamura, Rui,Shimizu, Hiroshi,Suzuki, Hitomi
, p. 261 - 266 (2007/10/02)
On treatment with tellurium tetrachloride in dichloromethane at room temperature, acetals and thioacetals are easily cleaved to regenerate original carbonyl compounds in good yields.
ClSiMe3 AS A REAGENT FOR THE CROTONIC CONDENSATION
Zav'yalov, S. I.,Dorofeeva, O. V.,Rumyantseva, E. E.
, p. 2163 - 2165 (2007/10/02)
Trmethylchlorosilane or a mixture of trimethylchlorosilane and zinc chloride may be used as reagents for the crotonic condensation of aldehydes with diethyl malonate and acetylacetone.The corresponding β-chloroketones were obtained upon the reaction of benzaldehyde with acetylacetone, acetophenone, and ω-bromoacetophenone in the presence of a mixture of trimethylchlorosilane and zinc chloride.
Organic Gas-Solid Reactions with Stilbenes, Chalcones, and Enamides
Kaupp, Gerd,Matthies, Doris
, p. 1897 - 1904 (2007/10/02)
Crystalline stilbene (1) adds gaseous chlorine and bromine without intermediate melting.The stereoselectivity is similar to that observed in solutions.Triphenylethene (3) also yields the products 4 in gas-solid reactions with chlorine and bromine, but these products tend to loose HX from the crystal; their conversion products are described.Neither crystalline 1 nor 3, but (E)-1,2-diphenyl-1-propene (7) adds gaseous hydrogen bromide regiospecifically.The same is true for the crystalline chalcone 10, which adds hydrogen bromide and -chloride selectively to give 11 nonisotypically.Gaseous ammonia reconverts crystalline 11 into 10.The enamide 12 in its crystalline state adds the gases hydrogen bromide, -chloride, methanethiol and hydrogen, to give the products 13, but also 15 (addition and condensation) and 16 (double addition). 13f which is formed via hydrogenation of crystals is not isotypical with its precursor 12.The liquid 17 crstallizes on freezing and then easily adds the gases hydrogen bromide (> - 50 deg C) and hydrogen chloride (> - 80 deg C) in highly controlled reactions to give the reactive compounds 18.These are converted not only into oligomers but also into the derivatives 19, 20, 21, and 22.The advantages of the unusual reaction procedures are discussed.
Friedel-Crafts Reactions of Some Vinyisilanes
Fleming, Ian,Pearce, Andrew
, p. 2485 - 2489 (2007/10/02)
Substituted cyclohexenylsilanes (2), (5), (9), and (13) undergo Friedel-Crafts reactions to give substitution products, site-selectively at the carbon atom carrying the trimethylsilyl group. β-Trimethylsilylstyrene (17) similary gives more substitution in Friedel-Crafts reactions with benzoyl chloride and with phenylacetyl chloride than styrene itself.The syntheses of the silanes are reported, and some limitations of the idea identified.
