Journal of the American Chemical Society p. 986 - 997 (1994)
Update date:2022-09-26
Topics:
RajanBabu
Nugent, William A.
Bis(cyclopentadienyl)titanium(III) chloride reacts with epoxides by initial C-O homolysis. The regiochemistry of the opening is determined by the relative stabilities of the radicals. Depending on the reaction partners, these radicals undergo intramolecular (hex-5-enyl cyclization) or intermolecular additions to olefins. The resultant radicals are efficiently scavenged by a second equivalent of Ti(III) to afford the corresponding Ti(IV) derivative. Treatment of this intermediate with electrophiles such as H+ or halogens provides a route to functionalized cyclopentanes and other useful products. The radical initially formed from an epoxide can also be trapped by H-atom donors such as 1,4-cyclohexadiene or tert-butyl thiol, resulting in an overall reduction of the epoxide. In the absence of a H-atom donor or an olefin, this radical is trapped by Ti(III), resulting in a β-oxido-Ti organometallic species which undergoes facile elimination to give an olefin. The reaction conditions are remarkably mild and are applicable to very sensitive substrates.
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Doi:10.1021/jo00091a013
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(1994)