Some reactions of ethyl azidoformate with quinones

Abstract

Ethyl azidoformate has been allowed to react with 1,4-naphthoquinone, 1,2-naphthoquinone, and 2-methoxy-1,4-naphthoquinone under different thermolytic conditions. A variety of products involving addition, substitution, insertion, and molecular rearrangement have been observed. The nature and yields of these products under different conditions are discussed inrelation to the mechanisms proposed for these reactions.

Synthesis of Some [1,3]Benzodioxoles via the Reaction of o-Quinones with Phosphorus Ylides

“…Obviously products 20-22 are the 5,5 -dimers of the expected, but not isolated or detected monomeric dioxoles 23a-c, respectively (Scheme 4), and were formed via dimerization of them, or, more probably, compounds 20-22 were produced from the reaction of the known 24 by dimerization of quinone 18 and the ylides. Although in other reactions of quinone 18 with some ylides, studied previously by us, only products of the monomeric quinone 18 were obtained, 4,10 the transformation of 18 into the bis-quinone 19 by its treatment with ethyl azidoformate also has been reported 24 without comments.…”

Electrogenerated superoxide anion: Hydroxylation of electroreducible substrates in aprotic solvent

“…Mp 188-190 °C, (Lit. [8] 192 ºC). 1 H RMN (300 MHz; CDCl 3 ) δ (ppm): 6.32 (s, 1H), 7.69 (td, J 1 =7.5 Hz, J 2 = 1.55 Hz, 1H), 7.78 (td, J 1 =7.5 Hz, J 2 = 1.25 Hz, 1H), 8.06 (t, J=1.55 Hz, 1H), 8.1 (t, J=1.25 Hz, 1H).…”