(η5-C5Me5)2(Me)TiOC(Me)CH2: titanum enolate or titanum alkoxide?

While proton and carbon NMR spectroscopy suggest that (Cp*)2(Me)TiOC(Me)CH2 (1, Cp* η5-C5Me5 is a typical titanum enolate, this material does not exhibit typical enolate reactivity. Specifically, 1 does not react with either methyl iodide or with benzaldehyde. However, some reagents that are typically used in electrophilic attack of metalalkyl or metalalkoxide bonds do react with 1. In some cases the electrophile displaces the enolate moeity, while in other cases selectivity for substitution of the titanium-bound methyl group is displayed. Thus the reactivity of 1 is more typical of that expected from a titanum alkoxide or an alkyl titanium rather than a titanium enolate. The possible use of the (Cp*)2(Me)Ti moiety as a protecting group for ketones is discussed.