Abstract
The stereochemistry of insertion reactions occurring at secondary carbon atoms bound to transition metals has been probed by examination of 13C and 1H spectra of 1,4-disubstituted cyclohexyl systems. The reaction of neat sulfur dioxide with cis and trans -4-methylcyclohexyl (pyridine)-cobaloxime leads to the trans and cis -4-methylcyclohexyl-S-sulfinate cobaloximes respectively, indicating inversion of configuration at the reacting carbon atom. A similar inversion is observed in the reaction of sulfur dioxide with [ cis-4-methylcyclohexyl Fe(CO) 2(η 5-C 5H 5)], but the triphenylphosphine-induced insertion of carbon monoxide in acetonitrile proceeds with retention of configuration.
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