Formation of carbenoid intermediates in the reaction of ditertiobutyl ketone with low-valent titanium reagents

Abstract

Abstract Treatment of t Bu 2 CO with TiCl 4 and Li(Hg) in THF gave the hydrocarbon t Bu 2 CH 2 as the major product (40% yield); 60% of the total quantity of t Bu 2 CH 2 was liberated after hydrolysis of the reaction mixture. Similar experiments with THF- d 8 and D 2 O afforded t Bu 2 CHD and t Bu 2 CD 2 , indicating that carbenoid species t Bu 2 C[Ti] are likely intermediates in the reaction of t Bu 2 CO with low-valent titanium reagents.