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Intramolecular reactivity of 1-alkoxyanthronylidenes. Disproportionation (SET) of carbene-derived 1,5-biradicals

✍ Scribed by Frank Gotzhein; Wolfgang Kirmse

Book ID: 104259775
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 195 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01398-7

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✦ Synopsis

Photolyses of 1-alkoxy-9-diazoanthrones 12 in benzene induce abstraction of hydrogen from the side chain, followed by cyclization (---) 15 --~ 16) or disproportionation (--~ 17 + 18) of the intervening biradicals 20. In alcohols, reduction of triplet anthronylidenes (314 ~ 21 ~ 22) competes with the formation of 20, and intramolecular electron transfer of 20 leads eventually to the acetals 24.

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