Reductive photocarboxylation of phenanthrene: A mechanistic investigation

AV Nikolaitchik, MAJ Rodgers…

Index: Nikolaitchik, Alexander V.; Rodgers, Michael A. J.; Neckers, Douglas C. Journal of Organic Chemistry, 1996 , vol. 61, # 3 p. 1065 - 1072

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Citation Number: 9

Abstract

Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N, N-dimethylaniline (DMA) produced 9, 10-dihydrophenanthrene-9-carboxylic acid (1) in 55% yield, trans-9, 10-dihydrophenanthrene-9, 10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N, N-dimethylamino) phenyl]-9, 10-dihydrophenanthrene-9-carboxylic acid (5). Addition of cumene, a hydrogen donor, or ...