Chloroacetonylation of C=C double bonds promoted by manganese(III) acetate

Dengiz, Çağatay
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.


Mn(OAc)(3)-promoted sulfur-directed addition of an active methylene compound to alkenes
DELIOMEROGLU, Murat K.; Dengiz, Çağatay; CALISKAN, Rasit; BALCI, METİN (2012-07-22)
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 mo...
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.
Manganese(III) acetate mediated oxidative coupling of phenylhdrazines with furan and thiophene
Emrullahoğlu, Mustafa; Demir, Ayhan Sıtkı; Department of Chemistry (2003)
A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.
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...
Functionalization of oxabenzonorbornadiene: Manganese(III)-mediated oxidative addition of dimedone
ÇALIŞKAN, Raşit; Sari, Ozlem; Balcı, Metin (Wiley, 2017-09-01)
3-Chloro-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)-3-hydroxy-5,5-dimethylcy-clohex- 2-en-1-one, synthesized by the reaction of oxabenzonorbornadiene with Mn(OAc)(3) and dimedone in the presence of HCl in acetic acid, was submitted to ring-opening reactions with BBr3 and H2SO4. Reaction with BBr3 yielded 2 products, a 5-membered ring and an 8-membered ring, with the former being the major product. However, the H2SO4-supported reaction exclusively formed an 8-membered ring. The mechanism of formation of th...
Citation Formats
Ç. Dengiz and M. BALCI, “Chloroacetonylation of C=C double bonds promoted by manganese(III) acetate,” TETRAHEDRON LETTERS, pp. 550–552, 2012, Accessed: 00, 2020. [Online]. Available: