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Bredt's rule

A double bond cannot be placed with one terminus at the bridgehead of a bridged ring system unless the rings are large enough to accommodate the double bond without excessive strain. For example, while bicyclo[2.2.1]hept-1-ene is only capable of existence as a transient, its higher homologues having a double bond at the bridgehead position have been isolated: e.g.
B00732
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1077
See also:
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2201
InChI=1/C9H14/c1-3-8-5-2-6-9(4-1)7-8/h3,9H,1-2,4-7H2
InChI=1/C9H14/c1-2-4-9-6-5-8(3-1)7-9/h5,9H,1-4,6-7H2
SIVKZPBURVINMX-UHFFFAOYAR
NCQNMEMRZWQKGX-UHFFFAOYAM
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Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.B00732.
Original PDF version: http://www.iupac.org/goldbook/B00732.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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