Tritium labelled alkenes via the Shapiro reaction
- Lawrence Berkeley Lab., CA (United States)
The authors report a simple synthesis of a variety of tritiated alkenes with high specific activity. The labelling steps involved in situ generation of the vinyllithium derivatives of the intermediate trisylhydrazone at low temperature, followed by quenching with high specific activity Tritiated water as an electrophile to generate the final tritiated alkenes. Several ketonic precursors with cyclopentanone and cyclohexanone rings, {alpha},{beta}-unsaturated and large ring cyclic ketones were selected and the corresponding trisylhydrazone derivatives were prepared. The Shapiro reaction conditions were optimized to work at a millimolar scale using deuteriated water as the electrophile. The successful reaction conditions were finally applied to the tritiation reactions. The chemical and radiochemical purity, and the specific radioactivity of the reaction products were determined by radio-hplc, gas chromatography and liquid scintillation counting as well as tritium NMR spectroscopy. The stereochemistry and specificity of tritium labelling was also established with tritium NMR spectroscopy. Application of different organolithium bases and the reaction mechanisms will be discussed.
- OSTI ID:
- 250144
- Report Number(s):
- CONF-9508100-; TRN: 96:002623-0082
- Resource Relation:
- Conference: 8. IUPAC symposium on organometallic chemistry directed towards organic synthesis, Santa Barbara, CA (United States), 6-10 Aug 1995; Other Information: PBD: 1995; Related Information: Is Part Of Eight IUPAC symposium on organometallic chemistry directed towards organic synthesis (OMCOS 8); PB: 375 p.
- Country of Publication:
- United States
- Language:
- English
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