Content:
Chapter 1 common and theoretical (pages 1–27): A. Y. Meyer
Chapter 2 Structural chemistry of enones (pages 29–54): Bernd Schweizer
Chapter three Conformations, chiroptical and similar spectral homes of enones (pages 55–105): Jacek Gawronski
Chapter four Thermochemistry of enones and comparable species (pages 107–128): Joel F. Liebman and Ralph M. Pollack
Chapter five NMR spectroscopy of enones (pages 129–150): Hugo E. Gottlieb
Chapter 6 The chemistry of ionized enones within the fuel part (pages 151–197): Frantisek Turecek
Chapter 7 Synthesis of enones (pages 199–280): Chachanat Thebtaranonth and Yodhathai Thebtaranonth
Chapter eight artificial makes use of of enones (pages 281–315): Gerhard V. Boyd
Chapter nine Acid–base behaviour of enones (pages 317–354): Romuald I. Zalewski
Chapter 10 Nucleophilic assaults on enones (pages 355–469): Daniele Duval and Serge Geribaldi
Chapter eleven Addition of electrons or radicals to ?, ??unsaturated ketones (pages 471–512): Glen A. Russell
Chapter 12 The response of enones with electrophiles (pages 513–558): Klaus Mullen and Peter Wolf
Chapter thirteen Chemical and enzymatic conversion of ?, ??enones to ?, ??enones (pages 559–597): Ralph M. Pollack, Patricia L. Bounds and Charles L. Bevins
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Extra resources for Enones: Volume 1 (1989)
Sample text
P. M. Vay, J . Chim. , 65, 2043, 2050 (1968). 82. K. Nishimoto and N. Mataga, Z. physik. , 13, 140 (1957). 83. R. B. Woodward, J . Am. Chem. , 63, 1123 (1941). 84. E. S. Stern and C. J. Timmons, Gillam and Stern’s Introduction to Electronic Absorption Spectroscopy in Organic Chemistry, 3rd edition, Arnold, London, 1970, pp. 78-88. 85. D. H. Williams and I. Fleming, Spectroscopic Methods in Organic Chemistry, 2nd edition, McGraw-Hill, London, 1973. 86. J. P. Flament and H. P. Gervais, J. Mol. , 90, 351 (1982).
Am. Chem. ,90, 2809 (1968). 104. A. Y. Meyer, unpublished work, referred to briefly in Reference 88. 105. A. Y. Meyer and R. Pasternak, Theor. Chim. Acta, 33, 215 (1974). The Chemistry of Enones Edited by S. Patai and 2. Rappoport 0 1989 John Wiley & Sons Ltd CHAPTER 2 Structural chemistry of enones BERND SCHWEIZER Institute of Organic Chemistry, ETH Zurich, CH-8092 Zurich, Switzerland I. INTRODUCTION . . . . . . 11. ENONES. . . . . . . . A. Acyclic Enones . . . . . . 1. Aliphatic acyclic enones .
085. Figure 1 shows a histogram of the C=C-C=O torsion angle of all acyclic enone fragments. As expected there is a preference for the enone group to be planar to allow a good delocalization of the n electrons. The dominant arrangement in the acyclic enone groups is apparently the s-cis conformation of the carbonyl and the double bond. 5 times as often as the s-trans form. Some of the structures have an 0-H or NH substituent at C(3) that can form a hydrogen bond to the carbonyl oxygen, which possibly favors the s-cis arrangement.