ISSN:
1434-193X
Keywords:
Radical reactions
;
Substituent effects
;
Nitrogen heterocycles
;
Dihydropyridines
;
Pyrrolines
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---A set of allene-tethered benzoyloximes (5) has been treated with nBu3SnH. Depending on their substitution pattern, a wide range of compounds has been obtained. If the stannyl radical adds on the allene, the C-centred radical thus formed undergoes either a 5-exo ring closure to give the cyclopentene derivatives 7 or a 6-endo ring closure onto the N atom to give the dihydropyridines 8. If the stannyl radical adds on the benzoyl moiety, an iminyl radical is formed which leads to the 3H-pyrroles 9 and the alkylidene-pyrrolines 10. Steric effects as well as polar effects are the factors governing the reaction course.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/2000/99373_s.pdf or from the author.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
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