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UBC Theses and Dissertations
Radiolabelling of organic molecules with short-lived radionuclides (¹¹C, ¹⁸F) Balatoni, Julius Alexander
Abstract
The primary aim of this study was to develop new methods for the introduction of short-lived radionuclides(11C, 18F) into organic molecules. This was accomplished by the use of organometallic intermediates: (i)(η6-arene)tricarbonylchromium complexes were used to facilitate aromatic nucleophilic substitution of the attached arene for the incorporation of [11C]cyanide anion, and (ii) vinyl-tin derivatives were employed for electrophilic fluorination reactions to produce 19F- and18F-labelled vinyl fluorides. A range of simple(η6-arene)tricarbonylchromium complexes were prepared as model systems. Fluorine was found to be the only leaving group that was readily displaced by cyanide. Non-radioactive and11C-labelled aryl nitriles were prepared in 10 minutes by reaction of complexes 1, 4, 5, and 6 with[12C]cyanide and[11C]cyanide in DMSO at elevated temperature. Under the reaction conditions used, the aryl nitrile product was liberated from the chromium tricarbonyl moiety thereby obviating the need for a separate oxidative decomplexation step. The reactivity of (E)-vinylstannanes 30, 31, 32, 33, and 34 was studied with elemental fluorine and acetyl hypofluorite under varied conditions. Generally, gaseous CH3COOF was found to be the most effective fluorinating agent for the electrophilic cleavage of vinyl-tin bonds. For example, 31 was fluorinated with CH3COOF, at room temperature, to yield an isomeric mixture of 39 and 40 in 41-42% yield; fluorination with F2 proceeded in 9.0% yield at best. Subsequently, 31 was radiofluorinated with CH3COO18F in 19% radiochemical yield (based on starting [18F]F2). [Scientific formulae used in this abstract could not be reproduced. Abstract also includes a figure.]
Item Metadata
Title |
Radiolabelling of organic molecules with short-lived radionuclides (¹¹C, ¹⁸F)
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
1994
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Description |
The primary aim of this study was to develop new methods for the introduction of short-lived
radionuclides(11C, 18F) into organic molecules. This was accomplished by the use
of organometallic intermediates: (i)(η6-arene)tricarbonylchromium complexes were used
to facilitate aromatic nucleophilic substitution of the attached arene for the
incorporation of [11C]cyanide anion, and (ii) vinyl-tin derivatives were employed for
electrophilic fluorination reactions to produce 19F- and18F-labelled vinyl fluorides.
A range of simple(η6-arene)tricarbonylchromium complexes were prepared as model
systems. Fluorine was found to be the only leaving group that was readily displaced by
cyanide. Non-radioactive and11C-labelled aryl nitriles were prepared in 10 minutes by
reaction of complexes 1, 4, 5, and 6 with[12C]cyanide and[11C]cyanide in DMSO at
elevated temperature. Under the reaction conditions used, the aryl nitrile product was
liberated from the chromium tricarbonyl moiety thereby obviating the need for a
separate oxidative decomplexation step.
The reactivity of (E)-vinylstannanes 30, 31, 32, 33, and 34 was studied with elemental
fluorine and acetyl hypofluorite under varied conditions. Generally, gaseous CH3COOF
was found to be the most effective fluorinating agent for the electrophilic cleavage of
vinyl-tin bonds. For example, 31 was fluorinated with CH3COOF, at room temperature,
to yield an isomeric mixture of 39 and 40 in 41-42% yield; fluorination with F2
proceeded in 9.0% yield at best. Subsequently, 31 was radiofluorinated with CH3COO18F
in 19% radiochemical yield (based on starting [18F]F2). [Scientific formulae used in this abstract could not be reproduced. Abstract also includes a figure.]
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Extent |
3457967 bytes
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Genre | |
Type | |
File Format |
application/pdf
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Language |
eng
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Date Available |
2009-06-04
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Provider |
Vancouver : University of British Columbia Library
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Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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DOI |
10.14288/1.0060503
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URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
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Graduation Date |
1995-05
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Campus | |
Scholarly Level |
Graduate
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Aggregated Source Repository |
DSpace
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Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.