Deciphering the mechanistic dichotomy in the cyclization of 1-(2-ethynylphenyl)-3, 3-dialkyltriazenes: competition between pericyclic and pseudocoarctate pathways

DB Kimball, TJR Weakley, R Herges…

Index: Kimball, David B.; Weakley, Timothy J. R.; Herges, Rainer; Haley, Michael M. Journal of the American Chemical Society, 2002 , vol. 124, # 45 p. 13463 - 13473

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Citation Number: 99

Abstract

The mechanistic aspects of the cyclization of (2-ethynylphenyl) triazenes under both thermal and copper-mediated conditions are reported. For cyclization to an isoindazole, a carbene mechanistic pathway is proposed. The carbene intermediate can react with oxygen, dimerize to give an alkene, or be trapped either intermolecularly (using 2, 3-dimethyl-2- butene to generate a cyclopropane) or intramolecularly (using a biphenyl moiety at the ...