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UCT Repository Prague MASTER THESIS

Studium nitrenové reaktivity diazirinů

A study of nitrenic reactivity of diazirines

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Ing. Petra Kolářová
UCT Repository Prague MASTER THESIS

Studium nitrenové reaktivity diazirinů

A study of nitrenic reactivity of diazirines

Circular user icon
Ing. Petra Kolářová

ANOTACE

Butyl-3-brom-3H-diazirin-3-karboxylát (2) nebo 3-brom-3-fenyl-3H-diazirin (10) reagují s fenylmagnesiumbromidem za přechodného vzniku 1-fenyl-1H-diazirinů 7a nebo 9a, které vykazují reaktivitu odpovídající imidoylnitrenům 7b nebo 9b (zachycení dalším ekvivalentem nukleofilu za vzniku N,N´-difenylamidinů 6 nebo 12, a C–H inzerce do diethyletheru poskytující N-fenylamidiny 4 a 5 nebo 13). Při reakci 3H-diazirinu 10 s kyanidovými ionty byla rovněž zaznamenána slabá nitrenová reaktivita 1-kyano-1H-diazirinu 37a (imidoylnitren 37b) poskytující N,N´-dikyanoamidin 36, zatímco při reakci 10 s methoxidovými ionty vznikající 1-methoxy-1H-diazirin17aneprojevuje reaktivitu odpovídající imid…

ANNOTATION

Butyl 3-bromo-3H-diazirine-3-carboxylate (2) or 3-bromo-3-phenyl-3H-diazirine (10) react with phenylmagnesiumbromide to give the intermediate 1-phenyl-1H-diazirines 7a or 9a exhibiting reactivity corresponding to imidoylnitrenes 7b or 9b (capture by another equivalent of nucleophile affording N,N´-diphenylamidines 6 or 12, and C–H insertion with diethylether affording N-phenylamidines 4 and 5, or 13). The reaction of 3H-diazirine 10 with cyanide ions also exhibited a weak nitrenic reactivity of 1-cyano-1H-diazirine 37a (imidoylnitrene 37b), affording N,N´-dicyanoamidine 36. 1-Methoxy-1H-diazirine17a, generated during the reaction of10with methoxide ions, doesn't show any reactiv…

Advisor
Ing. Tomáš Martinů, Ph.D.
Referee
doc. Ing. Stanislav Böhm, CSc.
Thesis type
Master thesis
Institution
University of Chemistry and Technology, Prague
Faculty
Faculty of Chemical Technology
Department
Department of Organic Chemistry
Study programme
Drug Synthesis
Specialization / field
Synthesis and Production of Drugs
MŠMT code
2801T018
Language
Czech
Resource accessibility
The printed version of the thesis is available at the department where the thesis was produced. Defence protocol and reviews are available at UCT Prague archive.
Access rights
open access
SIS ID
15711
Date available
Dec 5, 2013
Date modified
Dec 5, 2013
Date defended
Jun 3, 2013DEFENDED