Abstract
The photostimulated reaction of halonaphthalene with a series of carbanions derived from propionic acid derivatives in liquid ammonia led to the naphthylation at α-carbon of the carbanions in an isolated yield ranging from 25% to 86%. In all cases, the dehalonaphthalenes were found to be by-products and the reaction was inhibited by p-dinitrobenzene. An electron transfer from the carbanion to the halonaphthalene followed by ejection of halogen led to naphthyl radical, as predicted by comparing the LUMOs of the carbanions and the halonaphthalenes, was involved in the process. Absence of the alkylnaphthalene and 1,2-dinaphthylalkane in the products indicates the smooth electron transfer between (Naph-Nu)− and Naph-X. C-vs. O-naphthylation is fully addressed in terms of MNDO calculations and acid-base principle.
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