The oxo compound (C 5 Me 5 ) 2 TiO(pyr) ( 1 ) undergoes a 2 + 2 cycloaddition reaction with allene to give (Me 5 C 5 ) 2 Ti[OC(CH 2 )CH 2 ] ( 2 ), which contains a puckered TiOC 2 ring in the solid state. The metallacyclobutane 2 does not exchange with either free allene or pyridine on the NMR time scale and slowly converts to the ring-metalated product (C 5 Me 5 )(C 5 Me 4 CH 2 )Ti[OC(CH 2 )Me] ( 3 ) in solution and to the enolate complex (C 5 Me 5 ) 2 Ti[H][OC(CH 2 )Me] ( 4 ) in the presence of 1 atm of H 2 .
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Schwartz et al. (1996) studied this question.
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