Isotopic Scrambling and Mass Spectral Fragmentation Studies with 2-Ferrocenylethyl and 2-Ferrocenylethyl-1,1-D2 Systems

Abstract

In a number of reactions including the solvolysis of 2-ferrocenylethyl-1,1-d2 tosylate (1—OTs-1-d2) in 60% et OH, HCOOH, or CF3CH2OH, the reaction of 1—OH-l-d2 with SOCl2 in tetrahydrofuran or toluene, and the treatment of 1—Cl-1-d2 with AlCl3 in CH2Cl2, no scrambling of the D-label from C-1 to C-2 was observed, indicating the absence of any 1,2-ferrocenyl shifts in any of these SN1 type of reactions. In the mass spectral fragmentation of 1—X and 1—X-1-d2, where X = OTs, OH, OCHO, OCH2CF3 and Cl, a number of common features were observed, including [Formula: see text] and [Formula: see text]