Observation of catalytic aziridination in the presence of viologen additives

ORGN 525

Zheng Xue, zheng.xue@ttu.edu and Michael F. Mayer, mf.mayer@ttu.edu. Department of Chemistry and Biochemistry, Texas Tech University, Box 41061, Lubbock, TX 79409-1061
Tetracationic bisviologen cyclophane has been found to be an efficient additive in promoting aziridination of imines with phenyldiazomethane at room temperature. Both electron-rich and electron-deficient imine substrates were tested and found to undergo aziridination. A competition experiment with a known guest of the cyclophane significantly slowed the initial rate of reaction. A series of viologen additives were screened to probe the nature of catalysis. Comparison of the viologens reveals the tetracationic cyclophane to be the most efficient.