Synthetic, Sn-119 NMR Spectroscopic, Electrochemical, and Reactivity Study of Organotin A(3) Corrolates Including Chiral and Ferrocenyl Derivatives

Abstract

Various R/Ar-functionalized tin 5,10,15-tris-(pentafluorophenyl)corrolate derivatives are reported herein including the first ferrocenyltin corrolate species. The isopropyl, sec-butyl., 2-methyl-n-butyl-, phenyl-, 2-thienyl-, and ferrocenyltin species have been prepared and characterized through H-1, C-13, and Sn-119 HMQC NMR spectroscopy, mass spectrometry, UV-vis and photoluminescent spectroscopy, and cyclic voltammetry studies. J(C/H-Sn) NMR spectroscopic couplings and ring-current effects (upfield shifting) were determined for the R-Sn axial hydrogen and carbon atoms. This report adds to older conceptually similar reports, by, i.e., Janson et al. (J. Am. Chem. Soc. 1969, 91, 5210) and Walker et al. (J. Am. Chem. Soc. 1983, 105, 6923-6929), as discussed herein. Such NMR spectroscopic aspects are discussed for these model systems. Compound Sn-Ph bond cleavage was achieved by treatment with I-2.