Tetrahedron letters

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

F Gotzhein, W Kirmse

Index: Gotzhein, Frank; Kirmse, Wolfgang Tetrahedron Letters, 1998 , vol. 39, # 37 p. 6675 - 6678

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Citation Number: 2

Abstract

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.