Reactions of Neopentyl Bromide with Nucleophiles by the SRN1 Mechanism

Article abstract of DOI:10.1021/jo00215a029

The photostimulated reaction of neopentyl bromide (1) with benzenethiolate ion gave neopentyl phenyl sulfide in high yields.The photostimulated reaction of 1 with benzeneselenate ion gave neopentyl phenyl selenide, dineopentyl selenide, and diphenyl selenide but in low overall yields.The photostimulated reaction of 1 with diphenylphosphide and diphenylarsenide ions gave good yields of the substitution products.These reactions are slow in the dark and the photostimulated reactions are inhibited by radical scavengers such as di-tert-butyl nitroxide.All these resultssuggest that 1 reacts with these nucleophiles by the S_RN1 mechanism of nucleophilic substitution.