Skip to main content
. 2014 Jan 8;10:34–114. doi: 10.3762/bjoc.10.6

Table 13.

Examples of ozonides (1,2,4-trioxolanes) synthesized by the Griesbaum method.

Oxime 174 Ketone 175 Ozonolysis conditions 1,2,4-Trioxolane 176 Yield, % Ref.
graphic file with name Beilstein_J_Org_Chem-10-34-i158.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i159.jpg hexane, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i160.jpg 47–67 [256]
graphic file with name Beilstein_J_Org_Chem-10-34-i161.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i162.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i163.jpg 54 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i164.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i165.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i166.jpg 10–75 [91,94]
[95,296]
graphic file with name Beilstein_J_Org_Chem-10-34-i167.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i168.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i169.jpg 23–50 [91–93]
graphic file with name Beilstein_J_Org_Chem-10-34-i170.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i171.jpg pentane, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i172.jpg 48 [92–93]
graphic file with name Beilstein_J_Org_Chem-10-34-i173.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i174.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i175.jpg 32–58 [91–93]
graphic file with name Beilstein_J_Org_Chem-10-34-i176.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i177.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i178.jpg 20–70 [91–93,96]
[97,297]
graphic file with name Beilstein_J_Org_Chem-10-34-i179.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i180.jpg pentane, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i181.jpg 38 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i182.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i183.jpg pentane, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i184.jpg 41 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i185.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i186.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i187.jpg 33 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i188.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i189.jpg hexane, CH2Cl2,
0 °C		 graphic file with name Beilstein_J_Org_Chem-10-34-i190.jpg 17 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i191.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i192.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i193.jpg 27 [91]
graphic file with name Beilstein_J_Org_Chem-10-34-i194.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i195.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i196.jpg 53 [92–93]
graphic file with name Beilstein_J_Org_Chem-10-34-i197.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i198.jpg pentane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i199.jpg n.d.a [96–97]
graphic file with name Beilstein_J_Org_Chem-10-34-i200.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i201.jpg cyclohexane CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i202.jpg 30 [298]
graphic file with name Beilstein_J_Org_Chem-10-34-i203.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i204.jpg cyclohexane CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i205.jpg 54 [298]
graphic file with name Beilstein_J_Org_Chem-10-34-i206.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i207.jpg cyclohexane, CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i208.jpg 78 [258]

aYield was not determined