Allylic Strain

Allylic strain (also known as A1,3 strain, 1,3-allylic strain, or A-strain) in organic chemistry is a type of strain energy resulting from the interaction between a substituent on one end of an olefin with an allylic substituent on the other end. If the substituents (R and R') are large enough in size, they can sterically interfere with each other such that one conformer is greatly favored over the other. Allyic strain was first recognized in the literature in 1965 by Johnson and Malhotra. The authors were investigating cyclohexane conformations including endocyclic and exocylic double bonds when they noticed certain conformations were disfavored due to the geometry constraints caused by the double bond. Organic chemists capitalize on the rigidity resulting from allylic strain for use in asymmetric reactions.

Read more about Allylic StrainQuantifying Allylic Strain Energy, Influencing Factors

Other articles related to "allylic strain, strain":

Strain (chemistry) - Kinds of Strain - Van Der Waals Strain - Allylic Strain
... Allylic strain, or A1,3 strain is closely associated to syn-pentane strain ... An example of allylic strain can be seen in the compound 2-pentene ... usually take a more linear conformation to avoid the steric strain between the substituents ...
Application of Allylic Strain in Organic Reactions and Total Synthesis - Total Synthesis of Natural Products
... of (+)-monensin, Kishi and co-workers utilized the allylic strain to induce asymmetric induction in the hydroboration oxidation reaction ...

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