Intramolecular radical cyclisations to pyridines
Harrowven, D.C., Sutton, B.J. and Coulton, S. (2001) Intramolecular radical cyclisations to pyridines. Tetrahedron Letters, 42, (51), 9061-9064. (doi:10.1016/S0040-4039(01)01937-2).
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Description/Abstract
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.
| Item Type: | Article |
|---|---|
| Related URLs: | |
| Keywords: | radicals and radical reactions, pyridines, nitrogen heterocycles, cascade reactionscondensed thiophenes, toddaquinoline, substitution, rings |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19508 |
| Date Deposited: | 14 Feb 2006 |
| Last Modified: | 01 Jun 2011 08:33 |
| Contributors: | Harrowven, D.C. (Author) Sutton, B.J. (Author) Coulton, S. (Author) |
| Date: | 17 December 2001 |
| Status: | Published |
| Contact Email Address: | dch2@soton.ac.uk |
| URI: | http://eprints.soton.ac.uk/id/eprint/19508 |
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