Vol 13 Metal Carbenes In Organic Synthesis

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Volume Editors Professor Dr. K.H. Dötz Kekulé-Institut für Organische Chemie und Biochemie Rheinische Friedrich-Wilhelms-Universität Gerhard-Domagk-Strasse 1 53121 Bonn, Germany [email protected] Editorial Board Dr. John M. Brown Prof. Pierre H. Dixneuf Dyson Perrins Laboratory South Parks Road Oxford OX1 3QY [email protected] Campus de Beaulieu Université de Rennes 1 Av. du Gl Leclerc 35042 Rennes Cedex, France [email protected] Prof. Alois Fürstner Prof. Louis S. Hegedus Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 Mühlheim an der Ruhr, Germany [email protected] Department of Chemistry Colorado State University Fort Collins, Colorado 80523-1872, USA [email protected] colostate.edu Prof. Peter Hofmann Prof. Paul Knochel Organisch-Chemisches Institut Universität Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg, Germany [email protected] Fachbereich Chemie Ludwig-Maximilians-Universität Butenandstr. 5–13 Gebäuse F 81377 München, Germany [email protected] Prof. Gerard van Koten Prof. Shinji Murai Department of Metal-Mediated Synthesis Debye Research Institute Utrecht University Padualaan 8 3584 CA Utrecht, The Netherlands [email protected] Faculty of Engineering Department of Applied Chemistry Osaka University Yamadaoka 2-1, Suita-shi Osaka 565, Japan [email protected] Prof. Manfred Reetz Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 Mülheim an der Ruhr, Germany [email protected] Preface In 1915 a paper submitted to the Russian Physical and Chemical Society by L. Tschugajeff, professor at the Inorganic Division of the Chemical Institute of the University of St. Petersburg, stated that the reaction of a potassium chloroplatinum complex with methylisocyanide and hydrazine hydrate affords red shiny crystals; a careful and correct elemental analysis encouraged him to suggest the structure of a hydrazide-bridged platinum dimer. In 1968 – after E. O. Fischer’s pioneering rational synthesis and complete analytical characterization of carbonyl carbene complexes of chromium and tungsten – Tschugajeff ’s reaction was reinvestigated, and the complex was identified as a cyclic diaminocarbene coordinated to platinum. It revealed that by serendipity Tschugajeff had the first metal carbene complex in his hands, an idea which was beyond imagination in the early 1900’s. Indeed, metal carbene chemistry started in 1964 with