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Aryl radical-initiated cyclizations: Effect of aryl substituents on ring-size

✍ Scribed by Kathlyn A. Parker; Denice M. Spero; Karen C. Inman


Book ID
104218736
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
182 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


The pmence of a mdical rtabilizing group on the aql ring can lead to ring-expanded products.

Although radical cyclisation methodology is presently the subject of much attention by the synthetic chemistry community,1 studies of cyclizations initiated by aryl radicals2 have not been extensive nor have such cyclizations been exploited for total synthesis.


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Five aryl-substituted phenacetyl radicals (X = p-MeO, p-Me, H, p-Cl, p-CF 3 ) were generated by laser photolysis of the corresponding dibenzyl ketones in n-hexane and acetonitrile. The decarbonylation reaction was monitored through the rise in time-resolved absorption of the benzyl radical chromopho