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Volumn , Issue 22, 2004, Pages 4667-4671

2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

Author keywords

Azepine; Retro Friedel Crafts reaction; Ring opening; Small ring system

Indexed keywords

2,3,4 TRIPHENYL 3 AZABICYCLO[3.2.0]HEPTA 1,4 DIENE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; AZEPINE DERIVATIVE; BICYCLO COMPOUND; BUTANE; CYCLOBUTENE; UNCLASSIFIED DRUG;

EID: 12344305443     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400433     Document Type: Article
Times cited : (3)

References (35)
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    • The heats of formation of the carbocations 7 and 8 were obtained by use of the CAChe systems (Version 3.7, CAChe Scientific, Oxford Molecular Group) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Hearly, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; Heat of formation of cation 7: 331.63 kcal/ mol; heat of formation of cation 8: 311.62 kcal/mol; PM3: J. J. Stewart, J. Comp. Chem. 1989, 10, 209; Heat of formation of cation 7: 138.21 kcal/mol; heat of formation of cation 8: 120.12 kcal/mol.
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    • Dewar, M.J.S.1    Zoebisch, E.G.2    Hearly, E.F.3    Stewart, J.J.P.4
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    • The heats of formation of the carbocations 7 and 8 were obtained by use of the CAChe systems (Version 3.7, CAChe Scientific, Oxford Molecular Group) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Hearly, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; Heat of formation of cation 7: 331.63 kcal/ mol; heat of formation of cation 8: 311.62 kcal/mol; PM3: J. J. Stewart, J. Comp. Chem. 1989, 10, 209; Heat of formation of cation 7: 138.21 kcal/mol; heat of formation of cation 8: 120.12 kcal/mol.
    • (1989) J. Comp. Chem. , vol.10 , pp. 209
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    • The heats of formation of 13, 14, and 15 were obtained by use of the CAChe systems (Version 4.1.1, Oxford Molecular Group) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Hearly, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; 5a: 387.12538, 13: 29.70126, 14: 106.03925, 15: 65.75824, 16: 105.80957 kcal/ mol; PM3: J. J. Stewart, J. Comp. Chem. 1989, 10, 209; 5a: 350.41893, 13: 7.75890, 14, 55.42717, 15, 35.09190, 16: 78.16375 kcal/mol. As pointed out by one of the referees, there are great differences in the heats of formation of a single intermediate by different methods. These values are not absolute in nature but only of relative comparison.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Hearly, E.F.3    Stewart, J.J.P.4
  • 33
    • 84988129057 scopus 로고
    • The heats of formation of 13, 14, and 15 were obtained by use of the CAChe systems (Version 4.1.1, Oxford Molecular Group) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Hearly, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; 5a: 387.12538, 13: 29.70126, 14: 106.03925, 15: 65.75824, 16: 105.80957 kcal/ mol; PM3: J. J. Stewart, J. Comp. Chem. 1989, 10, 209; 5a: 350.41893, 13: 7.75890, 14, 55.42717, 15, 35.09190, 16: 78.16375 kcal/mol. As pointed out by one of the referees, there are great differences in the heats of formation of a single intermediate by different methods. These values are not absolute in nature but only of relative comparison.
    • (1989) J. Comp. Chem. , vol.10 , pp. 209
    • Stewart, J.J.1


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