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Mecanistic study on exchange between labeled cyanide and nitriles
Author(s) -
Hussain Munir,
Chaney James E.,
Digenis George A.,
Layton W. John
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580221002
Subject(s) - chemistry , nitrile , cyanide , yield (engineering) , borane , potassium cyanide , medicinal chemistry , nuclear chemistry , organic chemistry , catalysis , materials science , metallurgy
Abstract The potential of a clean, rapid exchange between the nitrile function of mandelonitrile and cyanide was examined for the preparation of labeled mandelonitrile which could be subsequently rapidly reduced with borane to labeled phenylethanolamine (PEOH). The mandelonitrile exchange (CN‐CN) was studied using [ 13 C]‐NaCN with crown ethers in THF, monitoring the results with 13 C‐NMR. A large increase in the intensity of the signal due to [ 13 C]‐nitrile was observed. The exchange was also carried out using [ 14 C]‐PEOH. The chemical Yield for the reduction of [ 14 C]‐mandelonitrile to [ 14 C]‐PEOH was 60% and the overall radiochemical yield of the cyanide‐exchange and borane reduction (based on [ 14 C]‐NaCN used) was 20%. Mechanisms are proposed which were found to be consistent with results of cyanide exchange of appropriately selected nitriles.