Wilzbach tritiation studies. II. stereospecificity in the tritiation of alcohols

Abstract

The mechanism of tritium labelling by the Wilzbach gas exposure method has been examined in terms of stereochemical effects on solid and liquid alcohols. Predominant retention of configuration is observed with (+)- and (-)-oct-2-yl hydrogen phthalate whilst octan-2-ol racemizes to the extent of 80%. Theories have been developed to explain the effect of phase on the extent of inversion and on the relatively fast rate of tritiation of the hydrogen attached to the asymmetric carbon of octan-2-ol, Aryl hydrogens of the esters tritiate ten times faster than alkyl hydrogens.