ISOMERIZATION OF CARYOPHYLLENE OXIDE CATALYZED BY SOLID ACIDS AND BASES

The reaction of caryophyllene oxide over eleven catalysts of solid acids and bases gave 4,5-dihydro-caryophyllen-5-one (III), (1R, 5S, 8R, 9R)-4,4,8-trimethyltricyclo[6.3.1.0(1,5)dodeca-2-en-9-o1 (IV), (2S, 5R, 9R)-caryophylla,1(12),8(15)-dien-9-ol (V), (2S, 5R, 9R)-caryophylla-1(12),7-dien-9-ol (VI), and (2S, 5R, 9S)-caryophylla-1(12)-7-dien-(9-ol (VII). A large amount of III as formed together with IV over FeSO4 and Zr-(SO4)2. Allylic alcohols (V, VI, and VII) were preferentially given by Al2O3-II and TiO2-ZrO2 in >74% selectivity: 96% on TiO2-ZrO2. Other catalysts formed three to five species of the products uniformly.