Experimental support for planar pseudopericyclic transition states in thermal cheletropic decarbonylations

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4289-4292

  Wei, Han Xun ^a   Zhou, Chun ^a   Ham, Sihyun ^a   White, Jonathan M ^b   Birney, David M ^a  

^a TEXAS TECH UNIVERSITY   (United States)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CARBONYLATION; CHEMICAL BOND; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; GEOMETRY; THERMAL ANALYSIS;

EID: 9444241501     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048197d     Document Type: Article

References (31)

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24. Compounds were synthesized as described in the literature or by analogy to related systems. See the Supporting Information for details of the synthesis and X-ray structure determination, CIF data have been deposited with CCSD, 252543-252549. (a) Roberts, E.; Turner, E. E. J. Chem. Soc. London 1927, 1832-1857. (b) Kollenz, G.; Igel, H.; Ziegler, E. Monatsh. Chem. 1972, 103, 450-459. (c) Kappe, C. O.; Terpetschnig, E.; Penn, G.; Kollenz, G.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Liebigs Ann. 1995, 537-543. (c) Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513-4525.
25. Compounds were synthesized as described in the literature or by analogy to related systems. See the Supporting Information for details of the synthesis and X-ray structure determination, CIF data have been deposited with CCSD, 252543-252549. (a) Roberts, E.; Turner, E. E. J. Chem. Soc. London 1927, 1832-1857. (b) Kollenz, G.; Igel, H.; Ziegler, E. Monatsh. Chem. 1972, 103, 450-459. (c) Kappe, C. O.; Terpetschnig, E.; Penn, G.; Kollenz, G.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Liebigs Ann. 1995, 537-543. (c) Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513-4525.
26. Compounds were synthesized as described in the literature or by analogy to related systems. See the Supporting Information for details of the synthesis and X-ray structure determination, CIF data have been deposited with CCSD, 252543-252549. (a) Roberts, E.; Turner, E. E. J. Chem. Soc. London 1927, 1832-1857. (b) Kollenz, G.; Igel, H.; Ziegler, E. Monatsh. Chem. 1972, 103, 450-459. (c) Kappe, C. O.; Terpetschnig, E.; Penn, G.; Kollenz, G.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Liebigs Ann. 1995, 537-543. (c) Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513-4525.
27. Compounds were synthesized as described in the literature or by analogy to related systems. See the Supporting Information for details of the synthesis and X-ray structure determination, CIF data have been deposited with CCSD, 252543-252549. (a) Roberts, E.; Turner, E. E. J. Chem. Soc. London 1927, 1832-1857. (b) Kollenz, G.; Igel, H.; Ziegler, E. Monatsh. Chem. 1972, 103, 450-459. (c) Kappe, C. O.; Terpetschnig, E.; Penn, G.; Kollenz, G.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Liebigs Ann. 1995, 537-543. (c) Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513-4525.
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30. This comparison is also validated by comparing 3 (N-Ph) with 4 (N-Pr); again, the N-Ph has the longer N1-C2 bond (1.395 vs 1.378 Å). (17) CSD Version 5.24 (Oct 2003): (a) Allen, F. H. Acta Crystallogr. 2002, B58, 380-388. (b) Allen, F. H.; Motherwell, W. D. S. Acta Crystallogr. 2002, B58, 407-422.
31. This comparison is also validated by comparing 3 (N-Ph) with 4 (N-Pr); again, the N-Ph has the longer N1-C2 bond (1.395 vs 1.378 Å). (17) CSD Version 5.24 (Oct 2003): (a) Allen, F. H. Acta Crystallogr. 2002, B58, 380-388. (b) Allen, F. H.; Motherwell, W. D. S. Acta Crystallogr. 2002, B58, 407-422.