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Bredts Rule (Ok) (Not happening). History and Background Discovered in 1924 by Julius Bredt while investigating the chemistry of naturally occurring bicyclic.

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Presentation on theme: "Bredts Rule (Ok) (Not happening). History and Background Discovered in 1924 by Julius Bredt while investigating the chemistry of naturally occurring bicyclic."— Presentation transcript:

1 Bredts Rule (Ok) (Not happening)

2 History and Background Discovered in 1924 by Julius Bredt while investigating the chemistry of naturally occurring bicyclic terpenes Hes German Bredt also was the first to determine the structure of camphor (1893) –Camphor contains a bridged ring

3 What It Says You cant 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

4 What It Says

5 What Its Good For Good for predicting the product resulting from elimination reactions of bridged ring systems + 0% NaOEt EtOH 110 o C Bredts Rule H H 100% H H H H Br H

6 Exceptions 8-membered rings with double bonds at the bridgehead can be isolated –Less than 7, extremely difficult to find said character

7 Exceptions Anti-Bredt Molecules –7 membered (or less) rings that do have double bonds located at the bridgehead –Example: 2- quinuclidonium tetrafluoroborate

8 Exceptions


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