The stereochemistry of organometallic compounds. Part III. Interactions of non-bonded substituents in the kinetically controlled reactions of substituted indanes with hexacarbonylchromium and tricarbonyl(trispyridine)chromium

Abstract

Reaction of tricarbonyl(trispyridine)chromium with 1- and 2-hydroxyindanes in the presence of boron trifluoride etherate gave in each case pure cis-tricarbonyl(hydroxyindane)chromium together with some pentacarbonyl(pyridine)chromium. 1-Methoxyindane also gave exclusively cis-tricarbonyl compound and the reactions have been shown to be kinetically controlled. These results are compared with the similar stereospecificity of the Simmons–Smith reaction with some hydroxy- and alkoxy-cyclic olefins. The early stages of the reaction of hexacarbonylchromium with hydroxy- and methoxy-indanes also appear to be partially kinetically controlled and the formation of cis-isomers is preferred. The reactions of tricarbonyl(trispyridine)chromium with other substituted indanes are discussed.