Topologically controlled coulombic interactions, a new tool in the developing of novel reactivity. photochemical and electrochemical cleavage of phenyl alkyl ethers

J Marquet, E Cayon, X Martin, F Casado…

Index: Marquet, Jorge; Cayon, Eduard; Martin, Xavier; Casado, Francisco; Gallardo, Iluminada; et al. Journal of Organic Chemistry, 1995 , vol. 60, # 12 p. 3814 - 3825

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Citation Number: 25

Abstract

The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested. Phenyl ethers substituted by electron- attracting groups do not undergo reductive fragmentation. However, related a-piperidino-w- (4-substituted-phenoxy)-alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is ...