Ferocenski acil-azidi, izocijanati i uree

master's thesis

• Title (english): Ferrocene acyl azides, isocyanates and ureas
• Author: Ivona Prešnjak
• Mentor: Vladimir Rapić (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2004-12, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Postupcima opisanim u literaturi pripravljene su ferocenske kiseline: ferocenkarboksilna kiselina (2, 80%), ferocenmaslačna kiselina (5, 80%) i 1'-metoksikarbonilferocen-1-karboksilna kiselina (12, 43%). Djelovanjem smjese NEt3/ClCOOEt, uz naknadni dodatak NaN3/H2O, ti su spojevi pretvoreni u odgovarajuće acil-azide 3 (35%), 6 i 13 (73%). Kod pretvorbe kiseline 5 uz azid 6 nastao je i izocijanat 7, a zagrijavanjem te smjese u benzenu dobiveno je 82% spoja 7. Na sličan način izvedene su pretvorbe azida u odgovarajuće izocijanate: 3 → 14 i 13 → 18. Tijekom 5-satnog zagrijavanja dobivene su smjese tih spojeva, a duljom reakcijom spojevi 3/14 i 13/18 pretvaraju se u sim-uree 16 i 19. Reakcijom smjesa 3/14 i 13/18, odn. izocijanata 7 s Ala-OMe dobiveni su konjugati 15 (23%), 20 (44%) i 17 (54%). Hidrolizom diester-uree 19 nastaje 93% dikiseline 21 koja je pretvorena u kiselinu-azid 22 (31%) i, nadalje, u kiselinu-izocijanat 24 (89%). Pokušaj pretvorbe dimera 24 u trimer 26 (koji sadrži 3 ferocenske jezgre povezane s 2 ureilenske razmaknice) nije uspio.

Abstract (english)

Ferrocene acids such as ferrocencarboxylic acid (2, 80%), ferrocenebutanoic acid (5, 80%) and 1'-methoxycarbonylferrocene-1-carboxylic acid (12, 43%) were prepared using methodes described in literature. By the action of NEt3/ClCOOEt with the subsequent addition of NaN3/H2O these acids were transformed into acyl-azides 3 (35%), 6 and 13 (73%). During the transformation of acid 5, azide 6 and isocyanate 7 arose together. Heating of these mixture in benzene gave 82% of isocyanate 7. In similar way transformations of azides into isocyanates were made: 3 → 14 and 13 → 18. During the 5 hour heating, mixture of those compounds grew up. If the reaction continued beyond this time, compounds 3/14 and 13/18 were transformed into sim-ureas 16 and 19. Reactions of 3/14, 13/18 and isocyanate 7 with Ala-OMe gave conjugates 15 (23%), 20 (44%) and 17 (54%). Hydrolysis of diester-urea 19 resulted in formation of 93% of diacide 21 which was transformed into acid-azide 22 (31%) and further into acid-isocyanate 24 (89%). The attempted transformation of dimer 24 into trimer 26 (wich include 3 ferrocene nucleuses connected with two ureyl interspaces) didn't succeded.

• Keywords: ferocenil-izocijanati; ferocenske sim-uree; ferocenski acil-azidi i konjugati s Ala
• Keywords (english): conugates with Ala; ferrocene acyl-azides; ferrocene sim-ureas and ferrocenyl isocyanates
• Language: croatian
• URN:NBN: urn:nbn:hr:159:525228
• Study programme: Title: Biotechnology; specializations in: Biochemical Engineering; Course: Biochemical Engineering; Study programme type: university; Study level: graduate; Academic / professional title: diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo (diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-09-12 10:51:28