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
Full Text: HTML
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.
Related Articles:
[Netka, Jill; Crump, Stephen L.; Rickborn, Bruce Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1189 - 1199]
[Zahn Chemische Berichte, 1934 , vol. 67, p. 2063,2071]