Journal of Organic Chemistry p. 2739 - 2742 (1985)
Update date:2022-09-26
Topics:
Pierini, Adriana B.
Penenory, Alicia B.
Rossi, Roberto A.
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 SRN1 mechanism of nucleophilic substitution.
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