Journal of Organic Chemistry p. 5963 - 5967 (1992)
Update date:2022-08-23
Topics:
Cremonini, Mauro A.
Lunazzi, Lodovico
Placucci, Giuseppe
Low-temperature photolysis of ArCH2OH derivatives (Ar = 2- and 3-furyl and -thienyl) in the presence of ButOOBut yields the corresponding ArCHOH radicals which can be observed by means of EPR spectroscopy.Each radical displays E and Z rotational conformers due to restricted Ar-Cα rotation.The study of ArCHOMe radicals, as well as of 2-furyl- and 2-thienylhydroxymethyl radicals having a methyl group in position 3 of the ring, allowed us to identify the most stable of the two conformers.The temperature dependence of the αOH hfs constant (assigned by deuterium substitution) has been interpreted on the basis of an averaging of ab initio αOH hfs constant over the rotation about the Cα-O bond which also allowed us to obtain an estimate of the corresponding rotation barrier.
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