Photosensitized Oxygenation of an Acyl Furan: Isolation of the First Furan Dioxetane by Rearrangement of its Endoperoxide and Selected Chemical Transformations | Zendy

Adam Waldemar | Zendy; Ahrweiler Michael | Zendy; Sauter Markus | Zendy

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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.

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