2-hidroksi-1,4-kinonların mangan(III) asetat aracılığıyla 2-tiyenil ve 2-furil sübstitüe alkenlerle radikalik halkalaşma reaksiyonları ve dihidrofurokinon bileşiklerinin sentezi

Bu calismada, elektrokimyasal yontemle sentezlenen MAH (mangan(III) asetat)’ in 2-hidroksi-1,4-naftakinon bilesikleriyle, heteroaromatik substitue alkenlerin tek elektron transferi (radikalik) mekanizmasi uzerinden yuruyen serbest radikalik halkalasma reaksiyonlari incelendi.Aktif metilen bilesigi olarak, 2-hidroksi-1,4-naftakinon (1a), 2-hidroksi-7-metil-1,4-naftakinon (1b), 5,7-dimetil-2-hidroksi-1,4-naftakinon (1c) ve 2-hidroksi-6-metoksi-1,4-naftakinon (1d) kullanildi. Doymamis substrat olarak kullanilan heteroaromatik substitue alkenler ise, 2-(1-fenilvinil)tiyofen (2a), 2-[1-(4-metilfenil)vinil] tiyofen (2b), 2-[1-(4-flourfenil)vinil]tiyofen (2c), 2-izopropeniltiyofen (2d), 2-[(E)-2-fenilvinil-1-metil–]tiyofen (2e), 2-[(E)-2-fenilvinil] tiyofen (2f), 2-siklopenten–1-iltiyofen (2g), 2-siklohekzen–1-iltiyofen (2h) ve 2-(1-fenilvinil)furan (2i) dir.2-hidroksi–1,4-naftakinon bilesiklerinin (1a, 1b, 1c ve 1d) MAH araciliginda heteroaromatik substitue alkenlere katilma reaksiyonlari sonucunda duzlemsel dihidrofuronaftakinon ve 3-alkenil–2-hidroksi–1,4-naftakinon bilesikleri elde edildi. Deneyler azot atmosferinde 60-70 oC sicaklikta gerceklestirildi. Elde edilen urunler kolon veya preparatif ince tabaka kromatografisi kullanilarak saflastirildi. Bilesiklerin yapilari; spektroskopik yontemler (IR, 1H-NMR, 13C-NMR, 19F-NMR ve kutle spektrumu) ve element analizi ile aydinlatildi.AbstractIn this study, the free radical cyclization reactions of 2-hydroxy-1,4-quinone compounds with olefines in electrochemical generated manganese(III) acetate were investigated.2-hydroxy -1,4-naphtaquinone (1a), 2-hydroxy -7-methyl–1,4- naphtaquinone (1b), 5,7-dimethyl-2-hydroxy-1,4-naphtaquinone (1c),2-hydroxy -6-methoxy–1,4- naphtaquinone (1d) were used as active methylene compounds and their reactions were performed with following olefines, 2-(1-phenylvinyl)thiophene (2a), 2-[1-(4-methylphenyl)vinyl] thiophene (2b), 2-[1-(4-fluorophenyl)vinyl]thiophene (2c), 2-isopropenylthiophene (2d), 2-[(E)-1-methyl-2-phenylvinyl]thiophene (2e), 2-[(E)-2 phenylvinyl] thiophene (2f), , 2-cyclopent-1-en-1-ylthiophene (2g), 2-cyclohex-1-en-1-ylthiophene (2h) and 2-(1-phenylvinyl)furane (2i) were used as olefines.In the free radical cyclization of 2-hydroxy–1,4-quinones lineer dihydrofuronaphtaquinones and 3-alkenyl–2-hydroxy–1,4-quinones were synthesized. The experiments were conducted under nitrogen atmosphere at 60–70 oC. Synthesized products were purified by column or preparative thin layer chromatography. The product structures were identified by spectroscopic methods (IR, 1H-NMR, 13C-NMR, 19F-NMR and mass spectra) and elemental analysis.