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Thermal reactions of santonic acid (1) in solution and flash vacuum pyrolysis were carried out in order to study the mechanism of formation of parasantonide (3) and santonide (4). Heating an acetic acid solution of 1 in a sealed tube at 200oC led to 3, while heating at 175 oC afforded 4. Flash vacuum pyrolysis of 1 was carried out between 300 and 550 oC, 10 torr and contact times of 10s. Results showed that 1 decomposed by at least two different mechanisms. One involving isomerization and lactonization affording 4 which affords 3 and the other involving radical scission and formation of aromatic and conjugated products. A mechanism involving isomerization to isosantonic acid (6) previous to lactonization is proposed for formation of 4.

Formation of santonide and parasantonide in the pyrolysis of santonic acid. A new insight of an old reaction