Decomposition Reaction of Longifolene Oxide, Isolongifolene Oxide and β-Caryophylene Oxide with Acids in the Presence of Synthetic Zeolites

Abstract

An investigation was made of the decomposition of longifolene oxide (1), isolongifolene oxide (2) and β-caryophylene oxide (3) with formic acid in the presence of synthetic zeolites (3A, 4A, 5A, 13 X, TSZ-320-REA, TSZ-330-HUA, TSZ-330-HSA, TSZ-600-HOA, TSZ-640-HOA and TSZ-640-NAA). With formic acid in 4A synthetic zeolite, the decomposition of (1) gave longicamphenilone (4) with high selectivity (86% at optimum). With formic acid in the presence of 13 X synthetic zeolite, isolongifolane-4-on (8) and isolongifolane-4-ol (9) were obtained as principal components from (2). The decomposition of (3) gave tricyclic compounds such as dihydroclovene-5-ol (14) as the major products.