Bredt’s Rule (Ok) (Not happening) History and Background • Discovered in 1924 by Julius Bredt while investigating the chemistry of naturally occurring bicyclic terpenes • He’s German • Bredt also was the first to determine the structure of camphor (1893) – Camphor contains a bridged ring What It Says • You can’t have a double bond connected to the bridgehead of a bridged ring system – UNLESS the ring is big enough • Having a double bond as part of the bridgehead would be the equivalent of having a trans double bond on the ring – This would create massive angular strain on the ring What It Says What It’s Good For • Good for predicting the product resulting from elimination reactions of bridged ring systems Bredt’s Rule H Br H H H H NaOEt + EtOH 110 oC 100% H 0% H Exceptions • 8-membered rings with double bonds at the bridgehead can be isolated – Less than 7, extremely difficult to find said character Exceptions • Anti-Bredt Molecules – 7 membered (or less) rings that do have double bonds located at the bridgehead – Example: 2quinuclidonium tetrafluoroborate Exceptions