4498-01-5Relevant academic research and scientific papers
Isolation of ozonides from gas-phase ozonolyses of terpenes
Griesbaum, Karl,Miclaus, Vasile,Jung, In Chan
, p. 647 - 649 (2007/10/03)
Ozonolyses of (-)-β-pinene (1) and of (+)-sabinene (6) in the gas phase afforded the corresponding ozonides 6,6- dimethylbicyclo[3.1.11,5]heptane[2-spiro-3]-1,2,4-trioxolane (2) and 5- isopropylbicyclo[3.1.01,5]hexane[2-spiro-3]1,2,4-trioxolane (7), which were isolated as mixtures of two diastereomers each. Major products were the corresponding ketones 6,6-dimethyl-2-oxobicyclo[3.1.11,5]heptane (3) and 5-isopropyl-2-oxobicyclo[3.1.01,5]hexane (8). Additional products were the lactones 7,7-dimethyl-2-oxa-3-oxobicyclo[4.1.11,6]octane (4) and 7,7- dimethyl-3-oxa-2-oxobicyclo[4.1.11,6]octane (5) derived from β-pinene (1) as well as 6-isopropyl-2-oxa-3-oxobicyclo[4.1.01,6]heptane (9) and 6- isopropyl-3-oxa-2-oxobicyclo[4.1.01,6]heptane (10) derived from sabinene (6). Ozonolyses of (-)-β-pinene (1) and of (+)-sabinene (6) in the gas phase afforded the corresponding ozonides 6,6-dimethylbicyclo[3.1.11,5]heptane[2-spiro-3]-1, 2,4-trioxolane (2) and 5-isopropylbicyclo[3.1.01,5]hexane [2-spiro-3]-1,2,4-trioxolane (7), which were isolated as mixtures of two diastereomers each. Major products were the corresponding ketones 6,6-dimethyl-2-oxobicyclo[3.1.11,5]heptane (3) and 5-isopropyl-2-oxobicyclo[3.1.01,5]hexane (8). Additional products were the lactones 7,7-dimethyl-2-oxa-3-oxobicyclo[4.1.11,6]octane (4) and 7,7-dimethyl-3-oxa-2-oxobicyclo[4.1.11,6]octane (5) derived from β-pinene (1) as well as 6-isopropyl-2-oxa-3-oxobicyclo[4.1.01,6]heptane (9) and 6-isopropyl-3-oxa-2-oxobicyclo[4.1.01,6]heptane (10) derived from sabinene (6).
