Boord olefin synthesis

The Boord olefin synthesis is an organic reaction forming alkenes from ethers carrying a halogen atom 2 carbons removed from the oxygen atom (β-halo-ethers) using a metal such as magnesium or zinc. The reaction, discovered by Cecil E. Boord in 1930 is a classic named reaction with high yields and broad scope.


 * [[Image:BoordReactionOverview.png|400px|The Boord olefin synthesis]]

The reaction type is an elimination reaction with magnesium forming an intermediate Grignard reagent. The alkoxy group is a poor leaving group and therefore an E1cB elimination reaction mechanism is proposed. The original publication describes the organic synthesis of the compound isoheptene in several steps.


 * [[Image:Boordreaction1930.png|Boord synthesis of isoheptene 1930]]

In a 1931 publication the scope is extended to 1,4-dienes with magnesium replaced by zinc (see also: Barbier reaction). In the first part of the reaction the allyl Grignard acts as a nucleophile in nucleophilic aliphatic substitution.


 * [[Image:BoordDieneReaction.png|500px|Boord diene synthesis 1931]]