Small Ring Compounds in Organic Synthesis VI pp 89-147

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 207)

Bicyclopropylidene — A Unique Tetrasubstituted Alkene and a Versatile C6-Building Block

  • Armin de Meijere
  • Sergei I. Kozhushkov
  • Alexander F. Khlebnikov
Chapter

Abstract

Strain in an organic molecule often correlates with increased reactivity, at least for certain types of reactions. Thus, the elucidation of the chemistry of highly strained alkenes like the unusual tetrasubstituted alkene, bicyclopropylidene (1), which is a particularly strained derivative of methylenecyclopropane (2), has proved to be fruitful both with respect to synthetic applications as a C6 building block, as well as understanding certain reaction principles. The different, steadily improved methods which have been developed for the preparation of this unusual alkene in the last thirty years as well as rather recent methods for the synthesis of functionally substituted, and spirocyclopropanated derivatives as well as bis(bicyclopropylidenyls) are presented. The special aspects of molecular geometry in bicyclopropylidenes as well as strain and its influence on chemical properties are discussed.The rich chemistry of bicyclopropylidene beginning with its well-known thermal rearrangement and dimerization, its dihalocarbene additions all the way to its recently developed organometallic chemistry, especially its reactions under the catalysis of palladium and other transition metals, is covered. Finally, some synthetically useful chemical transformations of bicyclopropylidene derivatives, e.g., synthetic approaches to the cyclopropanated analogs of natural products, are presented.

Keywords

Absolute configuration Amino acids Bicyclopropylidene Coupling reactions Cycloadditions Cyclopropanation Cyclopropanes Organolithium derivatives Palladium catalysis Radical reactions Small ring polycycles Spiro compounds Strain energy Sulfides 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Armin de Meijere
    • 1
  • Sergei I. Kozhushkov
    • 1
  • Alexander F. Khlebnikov
    • 1
  1. 1.Institut für Organische Chemie der Georg-AugustUniversität GöttingenGöttingenGermany

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