First preparation and isolation of a stable ferrocenylketene

2007 ARKIVOC  
Dedicated to Professor Ernst Anders on the occasion of his 65 th birthday, and in recognition of his early pioneering work on stereoselectivity in ketene reactions Abstract Ferrocenyl(triisopropylsilyl)ketene (6) is formed upon photolysis of the diazo ketone 5, and is the first example of an isolated ferrocenylketene. The X-ray structure of 6 shows that the ketenyl moiety is protected from both sides, by the ferrocenyl group and by the triisopropylsilyl group, respectively. The ketene is
more » ... he ketene is remarkably unreactive towards nucleophiles, and is less reactive towards 2 mM n-BuNH 2 than the parent ferrocenylketene by a factor of 7 x 10 8 , a result attributed to steric shielding to attack of the nucleophile, and the ketene stabilizing effect of the silyl substituent.
doi:10.3998/ark.5550190.0008.313 fatcat:s6lsxut6iraszfsqkbc5kw3g2q