2,2-BİS(2-FORMİLFENOKSİ)-4,4,6,6-BİS[SPİRO(2',2''-DİOXY-1',1''-BİFENİLİL)]SİKLOTRİFOSFAZENİN SCHİFF BAZI TÜREVLERİNİN SENTEZİ VE KARAKTERİZASYONU

Abstract

Hekzaklorosiklotrifosfazen(1) ile 2,2'-bifenol ile reaksiyona sokularak 2,2'-dikloro-4,4,6,6,-bis[spiro(2',2''-dioksi-1',1''-bifenilil)]siklotrifosfazen(2) elde edildi. Hekzaklorosiklotrifosfazen hava ve neme karşı hassas olduğu için bu reaksiyon havasız ortamda ve argon atmosferinde gerçekleştirildi. 2 bileşiği 2-hidroksibenzaldehit ile K2CO3'lı ortamda etkileştirilerek 2,2-bis(2-formilfenoksi)-4,4,6,6-bis[spiro(2',2''-dioksi-1',1''-bifenilil)]siklotrifosfazen(3) bileşiği elde edildi. Elde edilen 3 bileşiği aromatik primer aminlerle (Ar-NH2 veya Ar-CH2-NH2) etkileştirerek Schiff bazı taşıyan siklotrifosfazenler(4-13) elde edildi. Schiff bazı taşıyan 2,2-bis(2-formilfenoksi)(4-metoksibenzilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(4), 2,2-bis(2-formilfenoksi)(2-klorobenzilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(5), 2,2-bis(2-formilfenoksi)(4-klorobenzilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(6), 2,2-bis(2-formilfenoksi)(R-(+)-1-(2-naftil)etilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(7), 2,2-bis(2-formilfenoksi)(2-hidroksifenilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(8), 2,2-bis(2-formilfenoksi)(4-hidroksifenilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(9), 2,2-bis(2-formilfenoksi)(4-nitrilfenilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(10), 2,2-bis(2-formilfenoksi)(2-fenilfenilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(11), 2,2-bis(2-formilfenoksi)(2-hidroksi-4-klorofenilimin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(12) ve 2,2-bis(2-formilfenoksi)(piridin-2-imin)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''-bifenilil)siklotrifosfazen(13), bileşiklerinin sentezinde, sırasıyla 2-aminofenol, 4-aminofenol, 4-metoksibenzilamin, 2-klorobenzilamin, 4-klorobenzilamin, R-(+)-1-(2 Naftil)etilamin, 4-nitrilanilin, 2-fenilanilin, 2-amino-4-klorofenol, pirimidin-2-amin kullanılmıştır. Elde edilen ürünlerin yapıları IR, (1H, 13C, 31P) NMR ve elementel analiz ile aydınlatıldı. R(-)-1-siklohekziletilamin ve 4-metilbenzil amin ile 2,2-bis(2-formilfenoksi)-4,4,6,6,-bis[spiro(2',2''-dioxy-1',1''- bifenilil)siklotrifosfazen reaksiyonundan Schiff bazı elde edilemedi.ANAHTAR KELİMELER: Hekzaklorosiklotrifosfazen, fosfazen, schiff bazı, schiff bazı ve fosfazenler.In this study, hexachlorocylotriphosphazene(1) was reacted with biphenyl-2,2?-diol. From this reaction, 2,2-dichloro-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(2) was obtained. Since hexachlorocylotriphosphazene is sensitive to air and moisture, experimental studies were carried out at without air and moisture in argon atmosphere. 2,2-Bis(2-formilphenoxy)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(3) was synthesized from the reaction of (2) with 2-hydroxybenzaldehyde Schiff base containing 2,2-Bis(2-formilphenoxy)(4-methoxybenzylimin)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(4), 2,2-Bis(2-formilphenoxy)(2-chlorobenzylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(5), 2,2-Bis(2-formilphenoxy)(4-chlorobenzylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(6), 2,2-Bis(2-formilphenoxy)(R-(+)-1-(2-naphthylethylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(7), 2,2-Bis(2-formilphenoxy)(2-hydroxyphenylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(8), 2,2-Bis(2-formilphenoxy)(2-hydroxyphenylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(9), 2,2-Bis(2-formilphenoxy)(4-nitrilephenylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(10), 2,2-Bis(2-formilphenoxy)(2-phenylphenylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(11), 2,2-Bis(2-formilphenoxy)(2-hydroxy-4chlorophenylimine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene (12) and 2,2-Bis(2-formilphenoxy)(pyridine-2-imine)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene(13) were synthesized by the reaction of 2,2-Bis(2-formilphenoxy)-4,4,6,6,-bis[spiro(2?,2??-dioxy-1?,1??-bifenilyl)]cyclotriphosphazene (3) with 4-methoxy benzylamine, 2-chlorobenzylamine, 4-chlorobenzylamine, 2-naphthylethylamine, 2-hydroxyphenylamine, 2-hydroxyphenylamine, 4-nitrilephenylamine, 2-phenylphenylamine, 2-hydroxy-4chlorophenylamine and pyridine-2-amine, respectively. The structures of the compounds were characterized by IR, 1H, 13C and 31P NMR spectroscopy and elemental analysis. Schiff base compounds could not be obtained from the reaction of (3) with R-(-)-1-cyclohexylethanamine and 4-methylebenylamine.KEYWORDS: Hexachlorocyclotriphosphazene, phosphazene, schiff base, schiff base and phosphazenes