Photostimulated reactions of neopentyl halides with nucleophiles by the SRN1 mechanism

The photostimulated reaction of neopentyl halides with different nucleophiles by the SRN1 mechanism of nucleophilic substitution has been studied. Neopentyl halides do not react with carbon nucleophiles, diethylphosphite, diphenylphosphonite and azide ions, but they react with arsenide and selenide ions. The photostimulated reaction of neopentyl bromide with diphenylarsenide ions gave only the straightforward substitution product neopentyldiphenylarsine. On the other hand, the photostimulated reaction of bromobenzene with dineopentyl arsenide ions gave three arsines: dineopentylphenylarsine, neopentyldiphenylarsine and triphenylarsine. Neopentyl chloride reacts under irradiation with diphenylphosphide ions giving good yields of the substitution product.