Substitution reactions of nitrothiophenes. 6. Disparate mechanisms for substitution reactions at neopentyl carbons bearing 4-and 5-nitrothienyl groups

FI Flower, PJ Newcombe, RK Norris

Index: Flower, Felicity I.; Newcombe, Peter J.; Norris, Robert K. Journal of Organic Chemistry, 1983 , vol. 48, p. 4202 - 4205

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Citation Number: 9

Abstract

The reaction of the (5-nitro-2-thieny1)-and (4-nitro-2-thieny1) neopentyl chlorides (9 and 10) with p-toluenesulfinate, azide, and p-toluenethiolate ions proceeds smoothly and in high yield (70-95%) under mild conditions (20" C, Me2SO) to give the sulfones 14 and 15, the azides 16 and 17, and the sulfides 18 and 19, respectively. The mechanisms of these substitutions me quite different, however. The substitutions in the 5-nitro series take place ...