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J. Am. Chem. SOC.1995,117, 5375-5376 5375 Evidence for the Dominant Role of Secondary
 

Summary: J. Am. Chem. SOC.1995,117, 5375-5376 5375
Evidence for the Dominant Role of Secondary
Orbital Interactions in Determining the
Stereochemistryof the Diels- Alder Reaction: The
Case of Cyclopropenet
Yitzhak Apeloig* and Eynatte Matzner
Department of Chemistry
Technion-Zsrael Institute of Technology, Haifa 32000, Israel
Received January 18,1995
The Diels-Alder (DA) reaction is one of the most important
reactions both in synthesis and in its mechanisticimplications.Ia
Much attention was devoted to the facial stereoselectivity, Le.,
ex0 vs endo approach of the diene to the dienophile,Iafor which
cyclopropene (CP) is the simplest example (eq 1).
ex0
X X
endo
Alder rationalized the predominant endo selectivity in many
DA reactions (the "endorule") as due to "maximum accumula-
tion of unsaturation".Ib Woodward and Hoffmann2postulated

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry