The Boord olefin synthesis is an

organic reaction Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organ ...

forming

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s from

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

s carrying a

halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...

atom 2 carbons removed from the oxygen atom (β-halo-ethers) using a metal such as

magnesium Magnesium is a chemical element with the 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 of the periodic ta ...

zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc 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 periodi ...

. The reaction, discovered by

Cecil E. Boord Cecil Ernest Boord (June 29, 1884–November 3, 1969) was an American chemist. He graduated in 1907 from Wabash College and joined Ohio State University. He earned the titles of "dean of hydrocarbon chemistry" and "designer and builder of gasoli ...

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 A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...

. The alkoxy group is a poor leaving group and therefore an

E1cB elimination reaction The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group (such as -OH or -OR) is a relatively poor one. Usually a moderate t ...

mechanism is proposed. The original publication describes the

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

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. The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytic ...

; 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 , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

Grignard acts as a nucleophile in

nucleophilic aliphatic substitution In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The ...

. :

References

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