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Epoxidation of 2‐Methyl‐3‐phenylbenzofurans with Dimethyldioxirane: A Novel Reversible Valence Isomerization between Labile Benzofuran Epoxides and Quinone Methides, their Rearrangement, Methanolysis, and Cycloaddition Chemistry
Author(s) -
Adam Waldemar,
Hadjiarapoglou Lazaros,
Peters Karl,
Sauter Markus
Publication year - 1993
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.199307351
Subject(s) - isomerization , benzofuran , chemistry , dimethyldioxirane , cycloaddition , quinone , valence (chemistry) , photochemistry , epoxide , quinone methide , organic chemistry , medicinal chemistry , catalysis
That the labile benzofuran epoxides are difficult to observe is no longer surprising in view of the reversible valence isomerization between the benzofuran epoxides 2 and the quinone methides 3 described here. Compounds 2 and 3 were synthesized by epoxidation of 1 , and they show a wealth of reactions.