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- W2892307505 abstract "The tributyltin hydride/AIBN combination used to mediate radical cyclisations has become acommon protocol in organic chemistry. This system which allows good substrate flexibility is auseful complement to ionic annulation reactions. However, the tin residues are highly toxic anddifficult to separate from reaction mixtures. In this project, alternatives to tin have been usedwith varying success and a SPOS approach was adopted to minimise the problems associatedwith tin.Acyl radical addition to 2- and 3-substituted electron deficient pyrroles was used to construct avariety of interesting bicyclic compounds including pyrrolizine alkaloids nordanaidone andhydroxydanaidol. Acyl radical reduction was retarded by slow syringe-pump addition oftributyltin hydride in cyclohexane to the acyl selenide and AIBN in acetonitrile as a two-phasesolvent system. Carbon monoxide saturation of the reaction vessel and solution was alsonecessary to inhibit decarbonylation in slow cyclisations. [Continues.]" @default.
- W2892307505 created "2018-09-27" @default.
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- W2892307505 date "2002-01-01" @default.
- W2892307505 modified "2023-09-23" @default.
- W2892307505 title "Novel free radical protocols for the synthesis of heterocycles" @default.
- W2892307505 hasPublicationYear "2002" @default.
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