20294-40-0Relevant articles and documents
Formal radical closure onto aromatic rings-a general route to carbocycles
Clive, Derrick L. J.,Sunasee, Rajesh,Chen, Zhenhua
experimental part, p. 2434 - 2441 (2009/02/02)
A general method is described for indirectly effecting radical carbocyclization of an alkyl chain onto an aromatic ring. Birch reductive-alkylation of aromatic tert-butyl esters with α,ω- dibromides, chromium(vi)-mediated oxidation of the resulting 1,4-dienes and Finkelstein displacement of Br- with NaI gives cross-conjugated ketones that undergo radical cyclization. The products are easily aromatized to phenols by silylation, Saegusa oxidation and treatment with BiCl 3.H2O. A special feature of the route is that it allows attachment of a substituent to the original aromatic ring in place of the phenolic oxygen of the normal product.
