Mn(OAc)(3)-promoted sulfur-directed addition of an active methylene compound to alkenes

Dengiz, Çağatay
Various alkenes substituted at the 1,2-positions by phenyl, thiophene and furan rings were reacted with 3-(4-methoxyphenyl)-3-oxopropanenitrile in the presence of Mn(OAc)(3)center dot 2H(2)O. The exact structure and configuration of the dihydrofuran derivatives formed were determined. In all cases only one regioisomer was formed. The observed regioselectivity was explained on the basis of the formation of a complex between Mn(OAc)(3), alkene, and 3-(4-methoxyphenyl)-3-oxopropanenitrile, which directs the mode of the addition to the double bond.


Chloroacetonylation of C=C double bonds promoted by manganese(III) acetate
Dengiz, Çağatay; BALCI, METİN (2012-02-01)
The addition of acetylacetone to alkenes was performed using Mn(OAc)(3 center dot)2H(2)O in the presence of HCl. The intermediate formed was trapped by chloride. Removal of one of the acetyl groups with ammonia under very mild conditions provided compounds derived from chloroacetonylation of the double bonds.
Manganese(III) acetate mediated oxidation of N-methylindol and N-methylcarbazol derivatives
Demir, Ayhan S.; Tural, Servet (ARKAT USA, Inc., 2008-6-22)
Manganese(III) acetate mediated oxidation of 1-alkyl-1H-indole and 9-methyl-9H-carbazole was studied. 1-Methyl-1H-indole gives the 1-acetoxymethyl derivative with good yield. 1-Methyl- 2-phenyl-1H-indole furnished the oxidation of the methyl group and C-3 of indole to obtain the corresponding acetoxy derivatives. 1-ethyl-2-phenyl derivative only furnished the C-3 acetoxylation product. 1,2-Dimethyl-1H-indole furnished oxidation on both of the methyl groups. The major products are 1-methyl-1H-indole-2-carbal...
Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions
Demir, Ayhan Gürbüz (2008-06-30)
The alpha'-acetoxylation of enones and the alpha-acetoxylation of aromatic ketones were carried out with potassium permanganate and acetic acid, in which acetoxylation products were obtained in 74-96% yields. The same reaction was carried out with carboxylic acids other than acetic acid, which furnished corresponding acyloxy ketones with the same regioselectivity. For the first time, formyloxylation products were synthesized in a 61-85% yield by using formic acid. The potassium permanganate and acetic acid ...
Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of Mn(OAc)(3)
Sudemen, Mahir Burak; ZENGİN, MUSTAFA; GENÇ, HAYRİYE; Balcı, Metin (2011-01-01)
The reactions of some 1,3-dicarbonyl compounds with cycloheptatriene derivatives in the presence of Mn(OAc)(3) were examined. Cycloheptatriene forms mainly [2+3] and [6+3] dihydrofuran addition products derived from cycloheptatriene. However, the reaction of acetylacetone with cycloheptatriene substituted with an electron withdrawing group exclusively gave products derived from the norcaradiene structure. The formation mechanism of the products as well as the role of the substituent attached to cycloheptatr...
Manganese(III) acetate oxidation of some ketones in the presence of 3-chloropropionic acid and theoretical investigation of the products
Akdağ, Akın; Turker, L (2001-08-01)
Manganese(III) acetate oxidation of some ketones in the presence of 3-chloropropionic acid was carried out. The products were characterized. The experimental results were compared with the theoretical ones which was based on AM1 (UHF) type semi-empirical calculations. The theoretical results disfavor any mechanism solely based on radical stability involving radicals originating from the reactants.
Citation Formats
M. K. DELIOMEROGLU, Ç. Dengiz, R. CALISKAN, and M. BALCI, “Mn(OAc)(3)-promoted sulfur-directed addition of an active methylene compound to alkenes,” TETRAHEDRON, pp. 5838–5844, 2012, Accessed: 00, 2020. [Online]. Available: