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Russian Journal of Organic Chemistry

, Volume 49, Issue 7, pp 974–978 | Cite as

Thermal decomposition products of methyl 1,5-diphenyl- and 5-methyl-1-phenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-exo-carboxylates

  • V. V. Razin
  • M. E. Yakovlev
  • V. A. Vasin
Review
  • 50 Downloads

Abstract

Methyl 1,5-diphenyl- and 5-methyl-1-phenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-exo-carboxylates at 138°C undergo decomposition via elimination of nitrogen molecule with formation in each case of five products. Two products are methyl 1,3-diphenyl(or 1-methyl-3-phenyl)bicyclo[1.1.0]butane-2-endo- and -exo-carboxylates, and the three others are derivatives of buta-1,3-diene, methyl (Z)-2-benzylidene-3-phenyl(or 3-methyl)but-3-enoate and methyl (E)- and (Z)-3,4-diphenyl(or 4-methyl-3-phenyl)penta-2,4-dienoates. The formation of these products may be rationalized assuming intermediacy of substituted allylcarbene which undergoes both intramolecular cycloaddition and rearrangements involving 1,2-hydride and 1,2-vinyl shifts.

Keywords

Diene Thermolysis Product Thermal Decomposition Product Compound IIIb Endo Isomer 
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

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • V. V. Razin
    • 1
  • M. E. Yakovlev
    • 1
  • V. A. Vasin
    • 2
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Ogarev Mordovia State UniversitySaranskRepublic of Mordovia, Russia

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