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[11C]Carbon Monoxide in Palladium- / Selenium-Promoted Carbonylation Reactions: Synthesis of 11C-Imides, Hydrazides, Amides, Carboxylic Acids, Carboxylic Esters, Carbothioates, Ketones and Carbamoyl Compounds
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
2002 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

[11C]Carbon monoxide in low concentrations has been used in palladium- or seleniummediated carbonylation reactions such as the synthesis of 11C-imides, hydrazides, amides, carboxylic acids, esters, carbothioates, ketones and carbamoyl compounds.

In these reactions aryl iodides have been used in most cases. However, less reactive aryl triflate, chloride and bromides were activated using tetrabutylammonium iodide.

The reactivities of nucleophiles may have influence on the radiochemical yield of the 11Clabelled compounds. Carboxyamination of aryl halides using aniline derivatives yielded 10% of the corresponding 11C-amide. However, the radiochemical yields increased significantly when the aniline derivatives were treated with lithium bis(trimethylsilyl)amide. In contrast, this reagent did not improve the radiochemical yields when primary amines such as methylamine and benzylamine were used. In these cases the radiochemical yields were improved by using pempidine.

11C-Esterification usually gave low yields. However, the radiochemical yields of 11C-esters could be improved by using magnesium bromide and pempidine.

An excess of ligand may have a significant impact on palladium-promoted carbonylation reaction. The radiochemical yields of 11C-ketones were improved when using excess amounts of tri-o-tolylphosphine.

(13C)Carbon monoxide may be utilized for the synthesis of 13C-substituated compounds in order to confirm the position of 11C-labelling.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis , 2002. , s. 43
Serie
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 769
Emneord [en]
Organic chemistry
Emneord [sv]
Organisk kemi
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:uu:diva-2931ISBN: 91-554-5452-6 (tryckt)OAI: oai:DiVA.org:uu-2931DiVA, id: diva2:162162
Disputas
2002-11-29, Svedberg salen (kemikum), Uppsala, 10:15
Opponent
Tilgjengelig fra: 2002-11-06 Laget: 2002-11-06bibliografisk kontrollert

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