THERMOLYSIS OF THE BENZENE ANION-RADICAL 18-CROWN-6 COMPLEX

The C-O and C-H bonds of 18-crown-6 are activated when 18-crown-6 is c omplexed with the potassium salt of the benzene anion radical. Evacuat ed glass bulbs containing the solid anion radical salt of potassium 18 -crown-6 benzene anion radical were plunged into a bath at 320 degrees C, resulting in mini-explosions and generating a series of compounds including dioxane, 2-methyl-1,3-dioxolane, divinyl ether, hydrogen, me thane, and 15-crown-5. Deuterium labeling studies proved that all of t hese compounds originated from the 18-crown-6. Further, these labeling studies were an aid in discerning the mechanism of the decomposition. Benzene, 1,4-cyclohexadiene, and cyclohexene were also generated. The last two originated from the reaction of the anion radical of benzene with hydrogen.