商品簡介
Volume 78 in the venerable Organic Reactions series contains three chapters regarding the introduction (and in one case, removal) of nitrogen from organic compounds.
The first chapter by Aaron Wrobleski, Thomas C. Coombs, Chan Woo Huh, Sze-Wan Li and Jeffrey Aubé features a classic chemical reaction for introducing nitrogen into organic compounds, namely the Schmidt Reaction. This venerable reaction usually involves the combination of hydrazoic acid with aldehydes or ketones to generate amides. In fact The Schmidt Reaction was the subject of a previous chapter in Organic Reactions in Volume 3. Obviously, many new developments have appeared since 1946 and among the most synthetically useful are the reactions of alkyl azides with carbonyl compounds extensively developed in the Aubé laboratories.
The second chapter by William F. Berkowitz shines a spotlight on a less-well-known, though no less fascinating transformation that introduces nitrogen into organic compounds, The Neber Rearrangement. This unique chemical reaction also begins with ketones but provides the precious nitrogen atom, not from azide, but in the form of hydroxylamine that creates an oxime derivative.
The third chapter by Lynn James Guziec and Frank S. Guziec, Jr. describes an unusual class of reactions that involve the loss of small molecular fragments from a ring in service of uniting separate carbon atoms in that ring to form alkenes. These so called "extrusion reactions" are more commonly known for the loss of a single molecular fragment as in, e.g. the Ramburg-Bäcklund Reaction which has been reviewed twice in this series (L. Paquette, Volume 25 and R. J. K. Taylor and G. Casy, Volume 62). However, the chapter in this volume outranks the other extrusions in that two separate molecular fragments are lost with the formation of two new carbon-carbon bonds (twofold extrusion reactions).
作者簡介
Scott E. Denmark received his undergraduate degree from the Massachusetts Institute of Technology in 1975 and his graduate degree (D.Sc. Tech.) from the ETH-Zurich in 1980. He joined the faculty at Illinois in the same year. His research interests are in structural, synthetic and mechanistic organic chemistry.
目次
CHAPTER PAGE
1. THE SCHMIDT REACTIONAaron Wrobleski, Thomas C. Coombs, Chan Woo Huh, Sze-Wan Li, and Jeffrey Aub´e 1
2. THE NEBER REARRANGEMENT William F. Berkowitz 321
3. TWOFOLD EXTRUSION REACTIONSLynn James Guziec and Frank S. Guziec, Jr 411
CUMULATIVE CHAPTER TITLES BY VOLUME 551
AUTHOR INDEX, VOLUMES 1-78 567
CHAPTER AND TOPIC INDEX, VOLUMES 1-78 573
