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Additional recommended knowledge
The sulfone group contains an acidic proton in one of the α-positions which is abstracted by a strong base (scheme 1). The negative charge placed on this position (formally a carbanion) is transferred to the halogen residing on the other α-position in a nucleophilic displacement temporarily forming a three-membered cyclic sulfone. This intermediate is unstable and releases sulfur dioxide to form the alkene. Mixtures of cis isomer and trans isomer are usually obtained.
This reaction type gives access to 1,2-dimethylenecyclohexane (scheme 2):
The Favorskii rearrangement is a conceptually related reaction.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ramberg-Bäcklund_reaction". A list of authors is available in Wikipedia.|