Stereospecificity

In chemistry, stereospecificity is the property of a chemical reaction that yields different stereoisomeric reaction products from two stereoisomeric reactants depending on the reaction conditions.

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For example, the addition of dibromocarbene to cis-2-butene yields cis-2,3-dimethyl-1,1-dibromocyclopropane whereas addition of dibromocarbene to the trans isomer exclusively yields the trans cyclopropane.

Chiral synthesis is built on stereospecific reactions where also the optical activity of a chemical compound is preserved.

Another example is disrotatory ring closing reaction trans-cis-trans-2,4,6-octatriene to cis-dimethylcyclohexadiene.

See also

• Stereoselectivity
• Dynamic stereochemistry

References

• Skell, P.S. and Garner, A.Y. Journal of the American Chemical Society. 78, 3409 (1956)