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- W2950251412 abstract "Bis(cycIopentadienyl)titanium(III) chloride reacts with epoxides by initial C-0 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(II1) to afford the corresponding Ti(1V) 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(, resulting in a fl-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. The considerable utility of epoxides as building blocks for organic synthesis reflects both their ready availability and their ability to undergo selective nucleophilic substitution reactions (eq la) with predictable stereochemistry.' In contrast, the two-" @default.
- W2950251412 created "2019-06-27" @default.
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- W2950251412 date "2010-08-19" @default.
- W2950251412 modified "2023-09-27" @default.
- W2950251412 title "ChemInform Abstract: Selective Generation of Free Radicals from Epoxides Using a Transition- Metal Radical. A Powerful New Tool for Organic Synthesis." @default.
- W2950251412 cites W2095404450 @default.
- W2950251412 doi "https://doi.org/10.1002/chin.199424095" @default.
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