Deuterium and tritium labeling with the zinc-sodium iodide method

Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane. The method tolerates a variety of other reducible functionalities, namely, ..cap alpha..,..beta..-enone, ketone, and ester. The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens. The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts. The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group. Deuterium NMR spectra and their use in the configurational assignment are discussed.