THE OXYMERCURATION-DEMERCURATION OF CARYOPHYLLENES

Article abstract of DOI:10.1007/BF00580549

The oxymercuration-demercuration of caryophyllene (I) at a molar ratio of olefin to mercury salt of 1:2 has been performed.Using various chromatographic methods, the following substances have been isolated from the crude product: clovene (II), 1percent; caryophyllane 4,8-α-oxide (III), 52percent; 9-epicaryophyllane 4,8-β-oxide (IV), 11percent; caryolan-1-ol (V), 5.3percent; dihydrocaryophyllen-4α-ol (VI), 11percent; caryophyllan-4-ol 5,8-oxide (VII), 6.5percent; the symmetrical mercury derivative of the 9-epi-4,8-β-oxide (VIII), 2.1percent; and an unknown hydrocarbon, A, 1percent.The structure of the oxide (IV) has been established by x-ray structural analysis.