SRN1 Reactions in Nitrofuran Derivatives

Article abstract of DOI:10.1021/jo00389a028

The reaction of the sterically hindered neopentylic chloride 2-(1'-chloro-2,2'-dimethylpropyl)-5-nitrofuran (1) with p-toluenesulfinate azide, and p-toluenethiolate ions and the salts derived from 2-methylmalononitrile and 2-nitropropane proceed by the S_RN1 mechanism.The operation of this mechanism is confirmed by the inhibitory effect of oxygen, di-tert-butyl nitroxide, and galvinoxyl and the catalytic effect of irradiation by white light.Methoxide and thiocyanate ions do not bring about substitution on 1, and this and other evidence confirms that substitution isnot occurring by either S_N1 or S_N2 mechanisms.