Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of Mn(OAc)(3)

2011-01-01
Sudemen, Mahir Burak
ZENGİN, MUSTAFA
GENÇ, HAYRİYE
Balcı, Metin
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 cycloheptatriene is discussed.
TURKISH JOURNAL OF CHEMISTRY

Suggestions

Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines
Zora, Metin (Elsevier BV, 2007-10-15)
Synthesis of ferrocenyl-substituted pyrazoles via the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives is described. Depending upon the substitution pattern of hydrazine, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/ aryl-3-ferrocenylpyrazoles. The reaction appears to be general for a variety of hydrazine derivatives.
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives
Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
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.
Synthesis of 2,3-disubstituted thiophenes from ketoalkynes
Vatansever, Erol Can; Balcı, Metin; Department of Chemistry (2013)
Synthesis of thiophene containing compounds are of particular interest in synthetic organic chemistry. Besides the importance for synthetic organic chemistry, thiophene derivatives are used in applied research such as drug synthesis and study of functional materials. In this thesis, a new methodology for developing of 2,3-disubstituted thiophenes was developed. This methodology utilizes readily available compounds in a two-step synthesis to provide a facile access to the 2,3-disubstituted thiophenes. In the...
Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates
Polat-Cakir, Sidika; BEKSULTANOVA, Nurzhan; Doğan, Özdemir (Informa UK Limited, 2018-12-02)
A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.
Citation Formats
M. B. Sudemen, M. ZENGİN, H. GENÇ, and M. Balcı, “Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of Mn(OAc)(3),” TURKISH JOURNAL OF CHEMISTRY, pp. 1–11, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51591.