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 Magnesium is a chemical element; it has Symbol (chemistry), symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 ...

zinc Zinc is a chemical element; it has symbol Zn and atomic number 30. It is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic tabl ...

. The reaction, discovered by Cecil E. Boord in 1930 is a classic named reaction with high yields and broad scope.''Advanced Organic Chemistry'', 4th Edition, Jerry March, 1992. : 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. : In a 1931 publication''Nuclear syntheses in the olefin series II. 1,4-diolefins'' Bernard H. Shoemaker and Cecil E. Boord J. Am. Chem. Soc.; 1931; 53(4) pp 1505 - 1512; the scope is extended to 1,4-dienes with magnesium replaced by

(see also: Barbier reaction). In the first part of the reaction the

allyl In organic chemistry, an allyl group is a substituent with the structural formula . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...

Grignard acts as a nucleophile in nucleophilic aliphatic substitution. :

References

{{DEFAULTSORT:Boord Olefin Synthesis Olefination reactions Organic reactions Name reactions