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Practical approaches to labelling terminal alkynes with deuterium

Base catalysed exchange with sodium hydroxide, calcium oxide or N,N,N,N‐tetramethylguanidine in deuterium oxide is a viable procedure for the preparation of terminally deuterated alkynes for those alkynes stable to strong base. The use of silver perchlorate as a catalyst is an alternative practical...

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Detalles Bibliográficos
Autores principales: Chan, Melanie Y. T., Anwar, Arbab, Lockley, William J. S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303397/
https://www.ncbi.nlm.nih.gov/pubmed/35067956
http://dx.doi.org/10.1002/jlcr.3963
Descripción
Sumario:Base catalysed exchange with sodium hydroxide, calcium oxide or N,N,N,N‐tetramethylguanidine in deuterium oxide is a viable procedure for the preparation of terminally deuterated alkynes for those alkynes stable to strong base. The use of silver perchlorate as a catalyst is an alternative practical option when labelling alkynes which are sensitive to base or contain functionalities which would lead to labelling elsewhere in the molecule. Labelling with this catalyst takes place smoothly at ambient temperature in a mixture of N,N‐dimethylformamide and deuterium oxide.