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Boord olefin synthesis

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TheBoord olefin synthesis is anorganic reaction formingalkenes fromethers carrying ahalogen atom 2 carbons removed from the oxygen atom (β-halo-ethers) using a metal such asmagnesium orzinc. The reaction, discovered byCecil E. Boord in 1930[1] is a classicnamed reaction with high yields and broad scope.[2]

The Boord olefin synthesis

The reaction type is anelimination reaction with magnesium forming an intermediateGrignard reagent. The alkoxy group is a poorleaving group and therefore anE1cB elimination reaction mechanism is proposed.[2] The original publication describes theorganic synthesis of the compoundisoheptene in several steps.

Boord synthesis of isoheptene 1930

In a 1931 publication[3] the scope is extended to1,4-dienes with magnesium replaced byzinc (see also:Barbier reaction). In the first part of the reaction theallyl Grignard acts as a nucleophile innucleophilic aliphatic substitution.

Boord diene synthesis 1931

References

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  1. ^The synthesis of beta-bromo-alkyl ethers and their use in further synthesis Lloyd C. Swallen and Cecil E. BoordJ. Am. Chem. Soc.;1930; 52(2) pp 651 - 660;doi:10.1021/ja01365a033
  2. ^abAdvanced Organic Chemistry, 4th Edition, Jerry March,1992.
  3. ^Nuclear syntheses in the olefin series II. 1,4-diolefinsBernard H. Shoemaker and Cecil E. BoordJ. Am. Chem. Soc.;1931; 53(4) pp 1505 - 1512;doi:10.1021/ja01355a049
Alkenes
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Carbon-carbon
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Homologation reactions
Olefination reactions
Carbon-heteroatom
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Degradation
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Organic redox
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Rearrangement
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Ring forming
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Cycloaddition
Heterocycle forming reactions
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