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


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.


Diene Thermolysis Product Thermal Decomposition Product Compound IIIb Endo Isomer 
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© 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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