M. Lucarini et Gf. Pedulli, AN EPR STUDY OF THE REACTION OF TETRABUTYLAMMONIUM BOROHYDRIDE WITH N-HETEROCYCLES, Journal of organometallic chemistry, 494(1-2), 1995, pp. 123-131
The reactions between tetrabutylammonium borohydride and a series of n
itrogen-containing heteroaromatics bases have been investigated by ele
ctron paramagnetic resonance (EPR) spectroscopy. The radical anions of
the N-heterocycles, formed by a single electron-transfer process have
been observed with substrates having reduction potentials higher than
-1.2 V vs. SCE. With less reducible bases, the radical anions of the
adducts formed by complexation by one or two borane units of the nitro
gen atoms of the base were observed under photolytic conditions. This
is because the complexed N-heterocycles have larger electron affinitie
s than the starting base.