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A Non‐Stereospecific Diels–Alder Reaction
Author(s) -
Meier Herbert,
Eckes HeinzLudwig,
Niedermann HansPeter,
Kolshorn Heinz
Publication year - 1987
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.198710461
Subject(s) - diradical , stereospecificity , isomerization , chemistry , diels–alder reaction , cycloaddition , computational chemistry , double bond , organic chemistry , catalysis , physics , singlet state , nuclear physics , excited state
Deviations from the stereochemical norm are observed very seldomly for Diels‐Alder reactions ; since the discovery of this reaction, stereospecificity has been regarded as a basic feature of [4 + 2] cycloadditions. The non stereospecific course of the reaction shown below (e.g., R COOEt) is ascribed to the fact that the heterodiene initially forms only one bond with the dienophile. The resulting diradical can undergo subsequent isomerization.