The Journal of organic chemistry

Remarkable effect of water on functionalization of the phenyl ring in methyl-substituted benzene derivatives with F-TEDA-BF4

P Kralj, M Zupan, S Stavber

Index: Kralj, Petra; Zupan, Marko; Stavber, Stojan Journal of Organic Chemistry, 2006 , vol. 71, # 10 p. 3880 - 3888

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Citation Number: 14

Abstract

Various NF reagents reacted with hexamethylbenzene (1) forming side chain substituted alkoxides or esters in protic solvents, Ritter type side chain functionalization was observed in acetonitrile in the presence of trifluoroacetic acid, while in aqueous acetonitrile solution phenyl ring transformation took place, starting with ipso attack of water and further rearrangement of the methyl group as the main process. Rearranged 2, 3, 4, 5, 6, 6- ...