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antarafacial

   Also found in: Wikipedia 0.03 sec.
antarafacial [‚an·tə·rə′fā·shəl]
(organic chemistry)
The stereochemistry when, simultaneously, two sigma bonds are formed or broken on the opposite faces of the component pi systems, such as in a cycloaddition reaction.


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While the photochemical conversion formally presents an intramolecular ene process, the prospects of a concerted reaction would anticipate an antarafacial homo[1,5]-hydrogen shift, yielding the C-6 diastereomer.
As a result, the valence isomerization changes from being a thermally disfavored antarafacial [4n+2] electrocyclic ring closure (16 to 17) to a thermally favored suprafacial [4n+2] electrocyclic ring closure (19 to 20) [23].
 
 
 
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