Indanetricarbonylchromium: the effects of 1-syn- and 1-anti substituents on the regioselectivity of nucleophilic addition. Crystal structures of 1-syn- and 1-anti-methoxyindanetricarbonylchromium

Article abstract of DOI:10.1016/0022-328X(89)87025-1

A series of diastereomeric syn and anti Cr(CO)3 complexes of 1-substituted indanes have been prepared by thermolysis of Cr(CO)6 or by arene exchange with naphthalene-Cr(CO)3 (3).The regioselectivity of nucleophilic addition of α-nitrile carbon nucleophiles to syn and anti 1-R-indane Cr(CO)3 complexes (R=OMe 4, Me 10) has been investigated and compared with that of analogous reactions with indaneCr(CO)3 (1).The results of an X-ray study of syn- and anti-4 are presented.Nucleophilic additions are shown to be sensitive to the steric and electronic effects of the benzylic substituent and the nucleophile.When the reaction mixtures are warmed to 0 deg C, equilibration of the regioisomeric cyclohexadienyl intermediates takes place.