Harrowven, D.C., Sutton, B.J. and Coulton, S.
Intramolecular radical cyclisations to pyridines
Tetrahedron Letters, 42, (51), . (doi:10.1016/S0040-4039(01)01937-2).
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Intramolecular radical additions to the alpha-, beta- and gamma -carbons of a pyridine have each been shown to be facile processes. When a cis-alkene conjoins an ortho-iodoarene and a pyridine. radical cyclisation induced by homolysis of the carbon to iodine bond favours a 6-exo, endo-trig course. With a two carbon alkane conjoining the ortho-iodoarene and the pyridine, intermolecular hydrogen atom abstraction. 6-exo/endo-trig cyclisation and 5-exo-trig cyclisation modes compete. That the spirocyclic intermediates formed in the 5-exo-trig cyclisation rearrange with migration of the alkyl chain is noteworthy.
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