engleski

Termodinamic rearrangement of the pentacyclo[5.4.0.0(2, 6).0)3, 10).0(5, 9)] undecane skeleton

Reaction of pentacyclo[5.4.0.02, 6.03, 10.05, 9]undecane-8, 11-dione (1) with ethanedithiol, when performed in the presence of a Lewis acid catalyst (F3B-OEt2), afforded the corresponding mono(ethylene dithioacetal), 2, along with 7, 8-[(thioethano)thio]pentacyclo[6.3.0.02, 6.03, 10.05, 9]undecan-11-one mono(ethylene dithioacetal) (3). Raney nickel reduction of 2 resulted in hydrogenolysis of both the dithioacetal moiety and the cyclobutane ring in 2 and led to the formation of a 7, 8-[(thioethano)thio]pentacyclo[6.3.0.02, 6.03, 10.05, 9]undecane (11) in 35% yield.

Termodinamic rearrangement; pentacyclo[5.4.0.0(2; 6).0(3; 10).0(5; 9)] undecane

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