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Photosensitized Oxygenation of an Acyl Furan: Isolation of the First Furan Dioxetane by Rearrangement of its Endoperoxide and Selected Chemical Transformations
Author(s) -
Adam Waldemar,
Ahrweiler Michael,
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.199300801
Subject(s) - furan , dioxetane , chemistry , isomerization , photochemistry , valence (chemistry) , thermal decomposition , organic chemistry , catalysis , chemiluminescence
Surprisingly, the dioxetane 2 , the first isolated furan dioxetane, rearranges quantitatively into the spiroepoxide 3 with catalytic amounts of Et 4 NBr. The spiroepoxide also forms on thermolysis of the endoperoxide 1 and the dioxetane 2 . This valence isomerization is a new decomposition route for 1,2‐dioxetanes and offers a rational explanation for the formation of spiroepoxide‐like products from furan endoperoxides.