Saytzeff's rule is the result of empirical observations, and can be used to predict the outcome of elimination reactions. Now, ab initio calculations have provided the long-sought evidence to show that hyperconjugation is the key that unlocks the origin of this rule.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Saytzeff, A. M. Justus Liebigs Ann. Chem. 179, 296–301 (1875).
Hofmann, A. W. Ann. Chem. 78, 253–286 (1851).
Clayden, J., Greeves, N., Warren, S. & Wothers, P. in Organic Chemistry 489, 495 (Oxford Univ. Press, 2001).
Braida, B., Prana, V. & Hiberty, P. Angew. Chem. Int. Ed. 48, 5724–5728 (2009).
Lewis, E. D. J. Chem. Ed. 71, 93–97 (1994).
Markovnikov, V. Ann. Chem. 153, 228–259 (1870).
Hughes, P. J. Chem. Ed. 83, 1152–1154 (2006).
Mo, Y. et al. Angew. Chem. Int. Ed. 43, 1986–1990 (2004).
Gung, B. W. Tetrahedron 52, 5263–5301 (1996).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Webber, M., Spivey, A. Supporting Saytzeff. Nature Chem 1, 435–436 (2009). https://doi.org/10.1038/nchem.348
Issue Date:
DOI: https://doi.org/10.1038/nchem.348
