Evidence for the Möbius aromatic character of eight π electron conrotatory transition structure. Magnetic criteria
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 407-410
- https://doi.org/10.1039/p29940000407
Abstract
The Möbius aromatic character of the 8π electron transition structure for the conrotatory electrocyclic ring closure of (Z,Z)-octa-1,3,5,7-tetraene is demonstrated by downfield and upfield 1H chemical shifts as well as the enhanced magnetic susceptibility computed by the IGLO method. H1,8 (outer) are deshielded and H1,8 (inner) are shielded in the transition structure.Keywords
This publication has 24 references indexed in Scilit:
- A Detailed Theoretical Analysis of the 1,7‐Sigmatropic Hydrogen Shift: The Möbius Character of the Eight‐Electron Transition StructureAngewandte Chemie International Edition in English, 1993
- Eine detaillierte theoretische Analyse der 1,7‐sigmatropen Wasserstoffverschiebung: Der Möbius‐Charakter des Acht‐Elektronen‐ÜbergangszustandesAngewandte Chemie, 1993
- Electrocyclic reactions of 1-substituted 1,3,5,7-octatetraenes. An ab initio molecular orbital study of torquoselectivity in eight-electron electrocyclizationsJournal of the American Chemical Society, 1993
- Übergangsstrukturen in pericyclischen Reaktionen von KohlenwasserstoffenAngewandte Chemie, 1992
- Transition Structures of Hydrocarbon Pericyclic ReactionsAngewandte Chemie International Edition in English, 1992
- Moebius-Hueckel concept in organic chemistry. Application of organic molecules and reactionsAccounts of Chemical Research, 1971
- Zur stereospezifität der conrotatorischen cyclisierung des decatetraensTetrahedron Letters, 1969
- Zur kinetik der conrotatorischen valenzisomerisierung von stereoisomeren decatetraenenTetrahedron Letters, 1969
- Flash photolysis studies of 1,3,5-cyclooctatriene Reversible ring openingJournal of the American Chemical Society, 1967
- Hűckel molecular orbitals of Mőbius-type conformations of annulenesTetrahedron Letters, 1964