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Alkyliron- and Alkylcobalt Reagents, V.- Anticheleselective Cyanoalkylation with Cyanoalkyl Derivatives of Iron(II), Titanium(IV) and Further Transition Metals
Kauffmann, Thomas,Kieper, Hansjoerg
, p. 907 - 912 (2007/10/02)
In intermolecular competition experiments with substrate pairs which consist of a β-functionalized ketone and a normal ketone, cyanoalkyl derivatives of Fe, Ti, Cr, and Mn prefer in every case the normal ketone ("anticheleselectivity").NC-CH2Ti(OiPr)3 (4a) and NC-CH2FeCl (3a) are the best reagents for the anticheleselective transfer of the cyanomethyl group.For the anticheleselective transfer of the cyanoisopropyl group, NC-CMe2FeCl (3b) is superior to the corresponding Ti reagents.The ability of 4a as a highly anticheleselective cyanomethylating reagent has also been demonstrated with an intramolecular competition system (diketon 13).The reasons for the observed anticheleselectivity are discussed. Key Words: Organoiron compounds / Organotitanium compounds / Cyanoalkylation
