Combined oxygen-17 NMR spectra and oxygen-18 isotope effects in carbon-13 NMR spectra for oxygen labeling studies. Carbon .fwdarw. sulfur oxygen migration in the aqueous chlorination of mercapto alcohols

The application of this method is used to demonstrate both the presence and the absence of a carbon..-->..sulfur oxygen migration in the chlorination of mercapto alcohols, namely, 3-mercapto-1-propanol and 2-mercapto-1-ethanol in /sup 18/O labeled D/sub 2/O. The reaction products are of the first compound are CH/sub 2/-CH/sub 2/-CH/sub 2/-O-Schemically bondOchemically bondO, in which the endocyclic oxygen is labeled; and Cl(CH/sub 2/)/sub 3/SO/sub 2/Cl, in which the absence of an O label is noted. The chlorination of 2-mercapto-ethanol proceeds without intramolecular oxygen migration.