ORGANIC IONS IN GAS PHASE .21. SYNTHESIS AND MASS SPECTRA OF DEUTERIOTHIOPHENES

Mass‐spectral and n.m.r. analysis of thiophenes labeled by exchange with deuteriosulfuric acid establishes that exchange at the 2 and 5 positions is essentially complete before any deuterium is incorporated at positions 3 and 4. Thus, such exchange is a satisfactory procedure for position‐specific labeling. Mass spectra of the labeled thiophenes show that about 60% of the [CHS]+ ion yield is derived from molecular ions that have not undergone prior rearrangement. The remaining 40% arises by a path or paths in which the four hydrogen atoms lose position identity. Other decomposition paths contributing to the mass spectrum are characterized by more nearly complete scrambling of hydrogens. Copyright © 1969 John Wiley & Sons, Ltd.