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. 2014 Jan 8;10:34–114. doi: 10.3762/bjoc.10.6

Table 11.

Examples of 1,2,4-trioxolanes produced by the ozonolysis of alkenes.

Alkene 163 Ozonolysis conditions 1,2,4-Trioxolane 165 Yield, % Reference

graphic file with name Beilstein_J_Org_Chem-10-34-i024.jpg Et2O, −70 °C graphic file with name Beilstein_J_Org_Chem-10-34-i025.jpg 24 [270]
graphic file with name Beilstein_J_Org_Chem-10-34-i026.jpg Et2O, −70 °C graphic file with name Beilstein_J_Org_Chem-10-34-i027.jpg 27 [270]
graphic file with name Beilstein_J_Org_Chem-10-34-i028.jpg hexane, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i029.jpg 78 [256]
graphic file with name Beilstein_J_Org_Chem-10-34-i030.jpg hexane, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i031.jpg 73 [256]
graphic file with name Beilstein_J_Org_Chem-10-34-i032.jpg hexane, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i033.jpg 77 [256]
graphic file with name Beilstein_J_Org_Chem-10-34-i034.jpg hexane, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i035.jpg 61 [256]
graphic file with name Beilstein_J_Org_Chem-10-34-i036.jpg isooctane/CCl4, −78 °C, 1 h graphic file with name Beilstein_J_Org_Chem-10-34-i037.jpg >82 [271]
graphic file with name Beilstein_J_Org_Chem-10-34-i038.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i039.jpg 95 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i040.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i041.jpg 90 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i042.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i043.jpg 92 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i044.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i045.jpg 93 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i046.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i047.jpg 93 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i048.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i049.jpg 94 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i050.jpg pentane,
−78 °C
graphic file with name Beilstein_J_Org_Chem-10-34-i051.jpg 63 [272]
graphic file with name Beilstein_J_Org_Chem-10-34-i052.jpg freon-113, 15–20 °C, 2 h graphic file with name Beilstein_J_Org_Chem-10-34-i053.jpg The yield was not determined [273274]
graphic file with name Beilstein_J_Org_Chem-10-34-i054.jpg freon-113, 15–20 °C, 2 h graphic file with name Beilstein_J_Org_Chem-10-34-i055.jpg The yield was not determined [273]
graphic file with name Beilstein_J_Org_Chem-10-34-i056.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i057.jpg 96 [275]
graphic file with name Beilstein_J_Org_Chem-10-34-i058.jpg polymer-based, −78 °C, 8 h graphic file with name Beilstein_J_Org_Chem-10-34-i059.jpg 23 [276]
graphic file with name Beilstein_J_Org_Chem-10-34-i060.jpg polymer-based, −78 °C, 3 h graphic file with name Beilstein_J_Org_Chem-10-34-i061.jpg 38 [276]
graphic file with name Beilstein_J_Org_Chem-10-34-i062.jpg CH2Cl2, −70 °C graphic file with name Beilstein_J_Org_Chem-10-34-i063.jpg 48 [277]
graphic file with name Beilstein_J_Org_Chem-10-34-i064.jpg without solvent, −133 to −43 °C graphic file with name Beilstein_J_Org_Chem-10-34-i065.jpg 100 [278]
graphic file with name Beilstein_J_Org_Chem-10-34-i066.jpg 1) CH2Cl2,
−78 °C, 15 min.
2) Me2S, rt, 6 h
graphic file with name Beilstein_J_Org_Chem-10-34-i067.jpg 71 [279]
graphic file with name Beilstein_J_Org_Chem-10-34-i068.jpg hexane,
−78 °C, 30 min
graphic file with name Beilstein_J_Org_Chem-10-34-i069.jpg 6 [280]
graphic file with name Beilstein_J_Org_Chem-10-34-i070.jpg CH2Cl2, −78 °C, 20 min graphic file with name Beilstein_J_Org_Chem-10-34-i071.jpg The yield was not determined [281]
graphic file with name Beilstein_J_Org_Chem-10-34-i072.jpg CH2Cl2, −78 °C, 2 h graphic file with name Beilstein_J_Org_Chem-10-34-i073.jpg >97 [282]
graphic file with name Beilstein_J_Org_Chem-10-34-i074.jpg CDCl3, −65 °C graphic file with name Beilstein_J_Org_Chem-10-34-i075.jpg 88 [283]
graphic file with name Beilstein_J_Org_Chem-10-34-i076.jpg CFCl3, −70 °C graphic file with name Beilstein_J_Org_Chem-10-34-i077.jpg 100 [283]
graphic file with name Beilstein_J_Org_Chem-10-34-i078.jpg CH2Cl2, −78 °C, 1 h graphic file with name Beilstein_J_Org_Chem-10-34-i079.jpg 85 [284]
graphic file with name Beilstein_J_Org_Chem-10-34-i080.jpg CH2Cl2, −78 °C, 1 h graphic file with name Beilstein_J_Org_Chem-10-34-i081.jpg 70 [285]
graphic file with name Beilstein_J_Org_Chem-10-34-i082.jpg pentane,
−78 °C
graphic file with name Beilstein_J_Org_Chem-10-34-i083.jpg 10-30 [148152]
graphic file with name Beilstein_J_Org_Chem-10-34-i084.jpg Et2O/CH3OH, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i085.jpg 12 [254]
graphic file with name Beilstein_J_Org_Chem-10-34-i086.jpg CH2Cl2, −78 °C graphic file with name Beilstein_J_Org_Chem-10-34-i087.jpg 92 [286]
graphic file with name Beilstein_J_Org_Chem-10-34-i088.jpg CH2Cl2, 0 °C graphic file with name Beilstein_J_Org_Chem-10-34-i089.jpg 95 [287288]
graphic file with name Beilstein_J_Org_Chem-10-34-i090.jpg H2O/CH2Cl2,
0 °C
graphic file with name Beilstein_J_Org_Chem-10-34-i091.jpg 72 [289]
graphic file with name Beilstein_J_Org_Chem-10-34-i092.jpg 1) SiO2,
−78 °C;
2) Me2S, MeOH
graphic file with name Beilstein_J_Org_Chem-10-34-i093.jpg 30 [290]