Strain and Its Implications in Organic Chemistry

1. Front Matter

   Pages i-xviii

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2. Some Synthetic Implications of the Concept of Cyclopropyl Units as Pseudo-Functional Groups

   • Barry M. Trost

   Pages 1-23

3. Stereoselective Electrocyclizations and Sigmatropic Shifts of Strained Rings: Torquoelectronics!

   • Kendall N. Houk

   Pages 25-37

4. The Preparation and Thermal Rearrangement of Functionalized 6-(1-Alkenyl)Bicyclo[3.1.0]Hex-2-Enes. Applications to synthesis

   • Edward Piers

   Pages 39-50

5. Synthesis with Donor-Acceptor-Substituted Vinylcyclopropanes

   • H.-U. Reissig, R. Zschiesche, A. Wienand, M. Buchert

   Pages 51-58

6. Synthesis of Functionalized Episulfides

   • Wataru Ando, Norihiro Tokitoh

   Pages 59-75

7. Through-Bond Interaction Via Cyclobutane Relay Orbitals as a Means of Extending Conjugation

   • Leo A. Paquette, Jürgen Dressel

   Pages 77-107

8. [2+3] Carbo- and Hetero-Cyclic Annulation in the Design of Complex Molecules.1

   • T. Hudlicky, A. Fleming, T. Lovelace, G. Seoane, K. Gadamasetti, G. Sinai-Zingde

   Pages 109-115

9. Synthetic and Mechanistic Aspects of the Cyclopropene to Vinylcarbene Rearrangement

   • Mark S. Baird, Juma’a R. Al-Dulayymi, Helmi H. Hussain

   Pages 117-120

10. Generation and Interception of 1-Oxa-2, 3-Cyclohexadiene and 1,2,4-Cyclohexatriene

    • Manfred Christl, Martin Braun

    Pages 121-131

11. On the Relationship between Strain and Chemical Reactivity of Torsionally Distorted Carbon-Carbon Double Bonds

    • Kenneth J. Shea

    Pages 133-141

12. Photoinduced Single Electron Transfer from Strained Rings

    • Paul G. Gassman

    Pages 143-167

13. Chemical Behaviour of Cation Radicals Derived from Strained Molecules in Solution. Spiro-Activation in the Cleavage of Some Arylcyclopropanes Upon Treatment with TCNE or DDQ

    • Shinya Nishida

    Pages 169-176

14. The Cyclopropyl Group in Studies of Enzyme-Catalysed Reactions

    • C. J. Suckling

    Pages 177-205

15. Intramolecular [2+2] Cycloadditons of Ketenes and Olefins

    • Beat Ernst, Alain de Mesmaeker, Hans Greuter, Siem J. Veenstra

    Pages 207-234

16. Strained Iminium Salts in Synthesis

    • Léon Ghosez, Lian Yong Chen, Benoit Gobeaux, Cathy Houge, Istvan Marko, Matthew Perry et al.

    Pages 235-254

17. The Generation and Rearrangement of 2-Diazocarbonyl Cyclobutanones: The Formation of 5-Spirocyclopropyl-2 (5h) Furanones

    • R. D. Miller, W. Theis, G. Heilig, S. Kirchmeyer

    Pages 255-258

18. Computational Studies of Prismane, Helvetane/Israelane and Asterane

    • E. Ōsawa, J. M. Rudzinski, D. A. Barbiric, E. D. Jemmis

    Pages 259-261

19. Cyclobutane-Cyclopentane Interconversion of Coordinated Adducts of Cycloheptatriene and Tetracyanoethylene Via the [2,2]-Sigmahaptotropic Rearrangement

    • Zeev Goldschmidt, Hugo E. Gottlieb

    Pages 263-268

20. Quest for Higher Prismanes

    • Goverdhan Mehta

    Pages 269-281

The topic ·Stress and Strain· of this conference was ideally constrasted by the remoteness and quiet atmosphere of the meeting place Hotel Seehof In Ratzeburg, a small medieval town situated on a peninsula in lake "Kuchensee· east of Hamburg In northern Germany. With the participation of 53 leading experts from all over the world, the workshop covered the widest possible range from the advancement of bonding theory, new mechanistic insights into chemical transformations and physical properties of highly strained compounds to their use as building blocks In organic synthesis and even as probes Into the detection of enzyme mechanisms. Because of their specific reactivities small ring units can uniquely play their role in the construction of composite functionalities. Such functionalities can increase the elegance In natural and non-natural products syntheses, since they help to develop more convergent synthetic routes and Improve the necessary chemo-, regio-and stereo-selectivity. This book presents all of the 20 Invited lectures and is complemented with short versions of 12 contributed papers and 13 poster presentations. I am convinced that it will stimulate further rapid development of this field of organic chemistry, which recently has seen extensions into the bioorganic area as well as towards new materials. In fact, several ·supra-natural" -at first sight exotic -compounds are already available In useful quantities and are being exploited to create vastly new molecular devices, i. e. compounds with unprecedented molecular functions and polymers with unconventional properties.

• Cycloaddition
• Nucleophilic substitution
• Rearrangement
• bonding
• carbon
• catalysis
• metals
• natural product
• organic chemistry
• organic synthesis
• polymer
• structure
• synthesis

• Institut für Organische Chemie, Universität Hamburg, Hamburg, Germany

  Armin Meijere

• Institut für Organische Chemie, Universität Bonn, Bonn, Germany

  Siegfried Blechert

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