Premium
Tritium and deuterium labelling studies of alkali metal borohydrides and their application to simple reductions
Author(s) -
Than C.,
Morimoto H.,
Andres H.,
Williams P. G.
Publication year - 1996
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/(sici)1099-1344(199608)38:8<693::aid-jlcr883>3.0.co;2-4
Subject(s) - chemistry , deuterium , tritium , labelling , borohydride , borane , radiochemistry , reagent , hydrogen , nuclear magnetic resonance spectroscopy , deuterium nmr , mass spectrometry , organic chemistry , chromatography , catalysis , nuclear physics , biochemistry , physics
Simple and facile syntheses of highly deuterated and tritiated LiBH 4 , NaBH 4 and KBH 4 were achieved by hydrogen isotope exchange with deuterium or tritium gas at elevated temperatures. The exchange products were characterized by boron, proton and deuterium or tritium NMR spectroscopy. The extent of isotope ( 2 H or 3 H) incorporation was calculated from the patterns of 11 B NMR spectra. Several samples of tritiated NaBH 4 were treated with BF 3 ‐Et 2 O to produce tritiated borane‐THF complex, which is an electrophilic reducing agent. The utility of both the borohydride reagents and borane‐THF complex in labelling reactions was confirmed by exemplary reductions leading to specifically labelled products. The extent and orientation of labelling in the reduction products was assessed by a combination of radio‐HPLC analysis, 1 H, 2 H or 3 H NMR and mass spectrometry.