Decomposition of Several Sesquiterpene Oxides with Formic Acid in the Presence of Synthetic Zeolites

Abstract

Examination was made of the decomposition of ledene oxide (1), β-cedrene oxide (2) and humulene oxide (3) with formic acid in the presence of synthetic zeolites. The decomposition of (1) with formic acid in the presence of 1010 AH, 2020 AH, HSZ-330 HUA or HSZ-330 HSA zeolites afforded predominantly 5-isopropeny1-2, 8-dimethylbicyclo [5.3.0] dec-2-en-1-ol (4) in high conversion (83 % at optimum). The decomposition of (2) with formic acid in the presence of 2020 AH zeolite gave 2, 6, 6-trimethyltricyclo [5.3.1.01, 5] undecan-8-one (9) as a main product, or 74 % of all decomposition products. With 13 X zeolite, 2, 6, 6-trimethyltricyclo [5.3.1.01, 5] undeca-8-ene-8-carbaldehyde (10) was obtained as the main product with high conversion (71 % at maximum). The decomposition of (3) with formic acid in the presence of HSZ-600 HOA zeolite gave 4, 8, 11, 11-tetramethyltricyclo [6.3.0.02, 4] undec-9-en-5-ol (14), as the main product with high conversion (87 % at maximum).