The Journal of Organic Chemistry

Coupling of diazopurines, a curious steric effect in a free radical reaction

TC McKenzie, JW Epstein

Index: McKenzie, Thomas C.; Epstein, Joseph W. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4881 - 4884

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Citation Number: 35

Abstract

The reaction of adenine derivatives with nitrite esters in the presence of arenes was examined and found to give 6-arylpurines in good (83%) to poor (11%) yield. The arylated products consisted only of the meta and para isomers; none of the anticipated ortho isomers were found. The predominance of meta-and para-substituted producta is attributed to steric effects. The evidence that the reaction proceeds via a purine radical includes light ...