Nitrenes and Nitrenium Ions

DANIEL E. FALVEY, PhD, is Professor at the University of Maryland. His research focuses on reaction mechanisms and reactive intermediates, with an emphasis on the exploration of intermediates that play a role in biochemical processes. Dr. Falvey has been awarded the Merck Award and the Reynold C. Fuson Memorial Award in Chemistry. Acclaimed for his teaching abilities, he has received the Outstanding Teacher Award from the Center for Teaching Excellence. ANNA D. GUDMUNDSDOTTIR, PhD, is Professor of Chemistry at the University of Cincinnati. Dr. Gudmundsdottir's studies photo-removeable protecting groups, reactive intermediates, and polymer modification. Her research team elucidated the reactivity of triplet alkyl and vinyl nitrenes in solution and solid state using transient spectroscopy and matrix isolation. Among her many honors, Dr. Gudmundsdottir is a recipient of the NSF CAREER Award.

Preface to the Series vii Introduction ix Contributors xi 1 Ultrafast Time-Resolved Studies of the Photochemistry of Aryl Azides 1 Jin Wang, Gotard Burdzinski, and Matthew S. Platz 2 Theory and Computation in the Study of Nitrenes and their Excited-State Photoprecursors 33 Shubham Vyas, Arthur H. Winter, and Christopher M. Hadad 3 Nitrenium Ions and Related Species in Photoaffinity Labeling 77 R. Marshall Wilson and Valentyna Voskresenska 4 Aryl Nitrenium Ions in Aqueous Solution 117 Michael Novak and Yue-Ting Wang 5 Triplet Alkyl Nitrenes 167 Sivaramakrishnan Muthukrishnan, Ranaweera A. A. U. Ranaweera, and Anna D. Gudmundsdottir 6 Electronic Properties of Nitrenium Ions 191 Daniel E. Falvey 7 Time-Resolved Resonance Raman Spectroscopic Studies of Aryl Nitrenium Ions and their Chemical Reactions 217 David Lee Phillips 8 Matrix Studies on Aromatic and Heteroaromatic Nitrenes and their Rearrangements 273 Curt Wentrup 9 Nitreno Radicals 317 Dirk Grote and Wolfram Sander 10 Synthetic Applications of Nitrenium Ions 347 Duncan J. Wardrop and Edward G. Bowen 11 Fluorinated Aryl Nitrene Precursors 451 Elisa Leyva, Denisse de Loera, Socorro Leyva, and Rogelio Jimenez-Cata~no 12 Properties of Carbonyl Nitrenes and Related Acyl Nitrenes 481 Nina P. Gritsan Index 549