Free‐radical 4‐nitrophenylation of thieno[2,3‐b]pyridine. Part 3: Consideration of mechanistic and selectivity factors involved in the substitution process
Abstract:A 1:1 geometrically oriented encounter complex between thieno[2,3-b]pyridine (1) and 4-nitrophenyldiazoacetate (2) is proposed to account for the dominant formation (ca. 64%) of the 2-isomer in the mixture of 4-nitrophenyl-1 isomers obtained previously. A mechanism involving one-electron transfer from 1 to 2 plus fragmentation of 2 -• into 4-nitrophenyl free radical, N 2 , and acetate ion is invoked. Formation of other isomers is discussed.It is noted that there is a close correlation between orientational rul… Show more
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