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Mechanism of the Cycloaddition of Bicyclo[2.1.0]pent‐2‐ene: a Non‐concerted Homo‐Diels‐Alder Reaction
Author(s) -
Klärner FrankGerrit,
Naumann Manfred
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199010611
Subject(s) - bicyclic molecule , cycloaddition , tetracyanoethylene , chemistry , stereospecificity , concerted reaction , olefin fiber , ene reaction , pentane , medicinal chemistry , diels–alder reaction , reaction mechanism , stereochemistry , catalysis , organic chemistry
Tetracyanoethylene adds to bicyclo[2.1.0]pentenes 1 a, b in a stereospecific endo fashion . Therefore, the formal Diels–Alder reaction, like the [σ 2 + π 2 ] cycloaddition with bicyclo[2.1.0]pentane, presumably proceeds in two steps. The reaction with dicyanofumaric and dicyanomaleic esters is nonstereospecific with respect to the olefin components, thus supporting this supposition.