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The Role of Strain in the Homoaromatization of Semibullvalenes.
- Source :
-
Journal of Organic Chemistry . 4/21/2017, Vol. 82 Issue 8, p4136-4147. 12p. - Publication Year :
- 2017
-
Abstract
- The low activation barrier to the Cope rearrangement of semibullvalenes has been attributed to the inherent ring-strain of this nucleus. Appropriate, Dewar-Hoffmann, substitution of semibullvalene results in the stabilization of the transition state and a further lowering of the Cope barrier. An alternative proposal for lowering/eliminating this barrier is the use of strain to destabilize the localized semibullvalene. Using density functional and Hartree-Fock calculations, we predict that additionally straining the semibullvalene nucleus, by small ring annelations, will lead to a lowering of the Cope barrier and ultimately to ground state neutral homoaromatics. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 82
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 123620868
- Full Text :
- https://doi.org/10.1021/acs.joc.7b00043