Show simple item record

dc.contributor.advisorİbiş, Cemil
dc.contributor.authorÖzsoy Güneş, Zeliha
dc.date.accessioned2020-12-07T13:42:18Z
dc.date.available2020-12-07T13:42:18Z
dc.date.submitted2010
dc.date.issued2018-08-06
dc.identifier.urihttps://acikbilim.yok.gov.tr/handle/20.500.12812/153327
dc.description.abstractBu doktora tez çalışmasının amacı, geniş bir uygulama alanına sahip olan kinon bileşiklerinin S-, S,S-, S,O- nükleofilleri ile reaksiyonlarının incelenmesi ve bilinmeyen yeni tiyosübstitüe kinon bileşiklerinin sentezlenmesidir.Bu çalışmada, S-, S,S-, S,O- nükleofilleri ile halokinon bileşiklerinin çeşitli reaksiyonları sonucu bilinmeyen yeni sübstitüe kinon bileşikleri sentezlendi. Yeni kinon bileşiklerinin sentezlenmesinde; başlangıç maddesi olarak 2,3,5,6-tetrakloro-1,4-benzokinon (p-kloranil) (1a) ve 2,3-diklor-1,4-naftakinon (1b) bileşikleri kullanıldı.p-Kloranil (1a) bileşiğinin 4-florobenzil merkaptan ile sentez yöntemi 1'e göre reaksiyonundan yeni 2-kloro-3,5,6-tris(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (2), 2,3,5,6-tetrakis(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (3) ve 2-etoksi-3,5,6-tris(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (4) bileşikleri sentezlendi. p-Kloranil (1a) ile 4-florobenzil merkaptan'ın sentez yöntemi 2'ye göre olan reaksiyonundan yeni 2,5-dikloro-3,6-bis(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (5), 2,6-dikloro-3,5-bis(4-florobenzil tiyo)siklohekza-2,5-dien-1,4-dion (6), 2-kloro-3,5,6-tris(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (2) ve 2,3,5,6-tetrakis(4-florobenziltiyo)siklohekza-2,5-dien-1,4-dion (3) bileşikleri sentezlendi. Bilinmeyen yeni 6H,6H-dibenzo[1,2-b:4,5-e]bis[1,4]oksatiefin-6,14(8H,16H)-dion (7), 6H,6H-dibenzo[1,2-b:5,4-e]bis[1,4]oksatiefin-6,14(12H,16H)-dion (8) ve 2-etoksi-3,5,6-tris(2-(hidroksimetil)feniltiyo)siklohekza-2,5-dien-1,4-dion (9) bileşikleri p-kloranil (1a) ile 2-merkaptobenzil alkol bileşiklerinin reaksiyonundan sentez yöntemi 1'e göre elde edildi. p-Kloranil (1a) bileşiğinin 3-merkapto-1-propanol ile sentez yöntemi 1'e göre reaksiyonundan yeni 3,4,9,10-tetrahidro-2H,8H-benzo[1,2-b:4,5-b']bis[1,4]oksatiefin-6,12-dion (10), 3,4,9,10-tetrahidro-2H,8H-benzo[1,2-b:5,4-b']bis[1,4] oksatiefin-6,12-dion (11) ve 2-kloro-3,5,6-tris(3-hidroksipropiltiyo)siklohekza-2,5-dien-1,4-dion (12) bileşikleri sentezlendi. p-Kloranil (1a) ile, 1,6-hekzanditiyol'ün sentez yöntemi 1'ye göre olan reaksiyonundan yeni 10,11-dikloro-2,3,4,5,6,7-hekzahidro benzo[b][1,4]ditiesin-9,12-dion (13) bileşiği sentezlendi. Bilinmeyen yeni 2,3,4,5,6,7,8,9, 13,14,15,16,17,18,19,20-hekzadekahidrobenzo[1,2-b:4,5-b']bis[1,4]ditiasiklododesin-11,22 -dion (14) bileşiği p-kloranil (1a) ile 1,8-oktanditiyol bileşiklerinin reaksiyonundan sentez yöntemi 1'e göre elde edildi. p-Kloranil (1a) bileşiğinin siklopentil merkaptan ile sentez yöntemi 1'e göre reaksiyonundan yeni 2-kloro-3,5,6-tris(siklopentiltiyo)siklohekza-2,5-dien-1,4-dion (15), 2-kloro-3,6-bis(siklopentiltiyo)-5-etoksisiklohekza-2,5-dien-1,4-dion (16), 2,3,5,6-tetrakis(siklopentiltiyo)siklohekza-2,5-dien-1,4-dion (17), 2,5-bis(siklopentil tiyo)-3,6-dietoksisiklohekza-2,5-dien-1,4-dion (18) ve 2,6-bis(siklopentiltiyo)-3,5-dietoksi siklohekza-2,5-dien-1,4-dion (19) bileşikleri sentezlendi. p-Kloranil (1a) ile siklopentil merkaptan'ın sentez yöntemi 2'ye göre olan reaksiyonundan yeni 2,3,5-trikloro-6-(siklopentiltiyo)siklohekza-2,5-dien-1,4-dion (20), 2,5-dikloro-3,6-bis (siklopentiltiyo)siklo hekza-2,5-dien-1,4-dion (21), 2-kloro-3,5,6-tris(siklopentiltiyo)siklohekza-2,5-dien-1,4-dion (15) ve 2,3,5,6-tetrakis(siklopentiltiyo)siklohekza-2,5-dien-1,4-dion (17) bileşikleri sentezlendi. Bilinmeyen yeni 2,3,5,6-tetrakis(2,3,5,6-tetraflorofeniltiyo)siklohekza-2,5-dien-1,4-dion (22) ve 2,6-dietoksi-3,5-bis(2,3,5,6-tetraflorofeniltiyo)siklohekza-2,5-dien-1,4-dion (23) bileşikleri p-kloranil (1a) ile 2,3,5,6-tetrafloro benzentiyol bileşiklerinin reaksiyonundan sentez yöntemi 1'e göre elde edildi.2,3-Dikloro-1,4-naftakinon (1b) bileşiğinin 2,3,5,6-tetrafloro benzentiyol ile reaksiyonundan bilinmeyen yeni 2,3-bis(2,3,5,6-tetraflorofeniltiyo)naftalen-1,4-dion (24) ve 2-etoksi-3-(2,3,5,6-tetraflorofeniltiyo)naftalen-1,4-dion (25) bileşikleri sentezlendi. 2,3-Dikloro-1,4-naftakinon (1b) ile siklopentil merkaptan'ın reaksiyonundan bilinmeyen yeni 2,3-bis(siklopentiltiyo)naftalen-1,4-dion (26) ve 2-etoksi-3-(siklopentiltiyo)naftalen-1,4-dion (27) bileşikleri sentezlendi. Bilinmeyen yeni 2,3-bis(4-florobenziltiyo)naftalen-1,4-dion (28), 2-kloro-3-(4-florobenziltiyo)naftalen-1,4-dion (29) ve 2-etoksi-3-(4-florobenzil tiyo)naftalen-1,4-dion (30) bileşikleri 2,3-dikloro-1,4-naftakinon (1b) ile 4-florobenzil merkaptan'ın reaksiyonundan elde edildi.Sentezlenen yeni kinon bileşikleri kromatografik yöntemlerle saflaştırıldı. Bu bileşiklerin yapıları mikroanaliz ve spektroskopik yöntemler (IR, UV, 1H-NMR, 13C-NMR, MS) kullanılarak aydınlatıldı.
dc.description.abstractThe purpose of this doctoral thesis was to investigate the reactions of quinone compounds which has a wide application area with some S-, S,S-, S,O- nucleophiles and to synthesize unknown new thiosubstituted quinone compounds.In this study, the unknown new substituted-quinone compounds were synthesized by reactions of S-, S,S-, S,O- nucleophiles with haloquinones. 2,3,5,6-Tetrachloro-1,4-benzoquinone (p-chloranil) (1a) and 2,3-dichloro-1,4-naphthoquinone (1b) were used as starting materials to synthesis of new quinone compounds.Unknown new 2-chloro-3,5,6-tris(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (2), 2,3,5,6-tetrakis(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (3) and 2-ethoxy-3,5,6-tris(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (4) compounds were synthesized by reaction of p-chloranil (1a) with 4-fluorobenzyl mercaptan according to synthesis method 1. Unknown new 2,5-dichloro-3,6-bis(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (5), 2,6-dichloro-3,5-bis(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (6), 2-chloro-3,5,6-tris(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (2) and 2,3,5,6-tetrakis(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (3) compounds were synthesized by reaction of p-chloranil (1a) with 4-fluorobenzyl mercaptan according to synthesis method 2. Unknown new 6H,6H-dibenzo[1,2-b:4,5-e]bis[1,4]oxathiepin-6,14(8H,16H)-dione (7), 6H,6H-dibenzo[1,2-b:5,4-e]bis[1,4]oxathiepin-6,14(12H,16H)-dione (8) and 2-ethoxy-3,5,6-tris(2-(hydroxymethyl)phenylthio)cyclohexa-2,5-diene-1,4-dione (9) compounds were synthesized by reaction of p-chloranil (1a) with 2-mercaptobenzyl alcohol according to synthesis method 1. Unknown new 3,4,9,10-tetrahydro-2H,8H-benzo[1,2-b:4,5-b']bis [1,4]oxathiepin-6,12-dione (10), 3,4,9,10-tetrahydro-2H,8H-benzo[1,2-b:5,4-b']bis[1,4]oxa thiepin-6,12-dione (11) and 2-chloro-3,5,6-tris(3-hydroxpropylthio)cyclohexa-2,5-diene-1,4-dione (12) compounds were synthesized by reaction of p-chloranil (1a) with 3-mercapto-1-propanol according to synthesis method 1. Unknown new 10,11-dichloro-2,3,4, 5,6,7-hexahydrobenzo[b][1,4]dithiecine-9,12-dione (13) compounds were synthesized by reaction of p-chloranil (1a) with 1,6-hexanedithiol according to synthesis method 1. Unknown new 2,3,4,5,6,7,8,9,13,14,15,16,17,18,19,20-hexadecahydrobenzo[1,2-b:4,5-b'] bis[1,4]dithiacyclododecine-11,22-dione (14) compounds were synthesized by reaction of p-chloranil (1a) with 1,8-octanedithiol according to synthesis method 1. Unknown new 2-chloro-3,5,6-tris(cyclopentylthio)cyclohexa-2,5-diene-1,4-dione (15), 2-chloro-3,6-bis (cyclopentylthio)-5-ethoxycyclohexa-2,5-diene-1,4-dione (16), 2,3,5,6-tetrakis (cyclopentyl thio)cyclohexa-2,5-diene-1,4-dione (17), 2,5-bis(cyclopentylthio)-3,6-dietoksicyclohexa-2, 5-diene-1,4-dione (18) and 2,6-bis(cyclopentylthio)-3,5-diethoxycyclohexa-2,5-diene-1,4-dione (19) compounds were synthesized by reaction of p-chloranil (1a) with cyclopentyl mercaptan according to synthesis method 1. Unknown new 2,3,5-trichloro-6-(cyclopentyl thio)cyclohexa-2,5-diene-1,4-dione (20), 2,5-dichloro-3,6-bis(cyclopentylthio)cyclohexa-2, 5-diene-1,4-dione (21), 2-chloro-3,5,6-tris(cyclopentylthio)cyclohexa-2,5-diene-1,4-dione (15) and 2,3,5,6-tetrakis(cyclopentylthio)cyclohexa-2,5-diene-1,4-dione (17) compounds were synthesized by reaction of p-chloranil (1a) with cyclopentyl mercaptan according to synthesis method 2. Unknown new 2,3,5,6-tetrakis(2,3,5,6-tetrafluorophenylthio)cyclohexa -2,5-diene-1,4-dione (22) and 2,6-diethoxy-3,5-bis(2,3,5,6-tetrafluorophenylthio)cyclohexa -2, 5-diene-1,4-dione (23) compounds were synthesized by reaction of p-chloranil (1a) with 2,3,5,6-tetrafluoro benzenthiol according to synthesis method 1.Unknown new 2,3-bis(2,3,5,6-tetrafluorophenylthio)naphthalene-1,4-dione (24) and 2-ethoxy-3-(2,3,5,6-tetrafluorophenylthio)naphthalene-1,4-dione (25) compounds were synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1b) with 2,3,5,6-tetrafluoro benzenthiol according to synthesis method 1. Unknown new 2,3-bis(cyclopentylthio) naphthalene-1,4-dione (26) and 2-ethoxy-3-(cyclopentylthio)naphthalene-1,4-dione (27) compounds were synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1b) with cyclopentyl mercaptan according to synthesis method 1. Unknown new 2,3-bis(4-fluoro benzylthio)naphthalene-1,4-dione (28), 2-chloro-3-(4-fluorobenzylthio)naphthalene-1,4-dione (29) and 2-ethoxy-3-(4-fluorobenzylthio)naphthalene-1,4-dione (30) compounds were synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1b) with 4-fluorobenzyl mercaptan according to synthesis method 1.The novel synthesized quinone compounds were purified by chromatographic methods. The structures of compounds were determined by using micro analysis and spectroscopic methods (IR, UV, 1H-NMR, 13C-NMR, MS).en_US
dc.languageTurkish
dc.language.isotr
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rightsAttribution 4.0 United Statestr_TR
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectKimyatr_TR
dc.subjectChemistryen_US
dc.titleHalokinonların S-, O- ve N- nükleofilleri ile reaksiyonlarından bazı yeni kinon boyalarının sentezi
dc.title.alternativeThe synthesis of the some new quinone dyes from the reactions of haloquinones with S-, O- and N- nucleophiles
dc.typedoctoralThesis
dc.date.updated2018-08-06
dc.contributor.departmentKimya Anabilim Dalı
dc.subject.ytm1,4-benzoquinone
dc.identifier.yokid390857
dc.publisher.instituteFen Bilimleri Enstitüsü
dc.publisher.universityİSTANBUL ÜNİVERSİTESİ
dc.identifier.thesisid282769
dc.description.pages215
dc.publisher.disciplineOrganik Kimya Bilim Dalı


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record

info:eu-repo/semantics/openAccess
Except where otherwise noted, this item's license is described as info:eu-repo/semantics/openAccess