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

  • Manfred Christl
  • Martin Braun
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

The cycloadducts 6 and 7 of tricyclo[4.1.0.02-7]-hepta-3, 4-diene (5) with styrene and 1,3-butadiene rearrange to unusual products on thermolysis, namely the cyclohepta- triene derivatives 9 and 10. l-Oxa-3,4-cyclohexadiene (20) is generated smoothly from 6, 6-dichloro-3-oxabicyclo[3.1.0]- hexane (22)and n-butyllithium. l-Oxa-2,3-cyclohexadiene (21) is formed from 6-exo-bromo-6-endo-fluoro-2-oxabicyclo- [3.1.0]hexane (30) and methyllithium. In the presence of activated olefins, this reaction provides an efficient route to 28 and 33 - 38,the trapping products of 21.Intere- stingly, [2+2]-cycloadditions do not take place at the same double bond of 21 as [4+2]-cycloadditions. The reactions of 1,3-cyclopentadiene and indene with bromofluorocarbene af- ford 6-exo-bromo-6-endo-fluorobicyclo[3.1.0]hex-2-ene (50) and its benzo derivative 45, respectively. On treatment of these compounds with methyllithium in the presence of sty- rene, the interception products 53 and 47 of 1, 2, 4-cyclo- hexatriene (44) and its benzoderivative 43,respectively, are formed in good yields.

Keywords

Lithium Atom Lithium Fluoride Trapping Product Monium Chloride Trapping Reaction 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Manfred Christl
    • 1
  • Martin Braun
    • 1
  1. 1.Institut für Organische Chemieder Universität WürzburgWürzburgFederal Republic of Germany

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