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

Table 23.

Examples of 1,2,4-trioxanes 357 synthesized based on epoxides 355.

Epoxide 355 Carbonyl compound Reaction conditions 1,2,4-Trioxane 357 Yield
i) 356
ii) 357, %
Ref.

graphic file with name Beilstein_J_Org_Chem-10-34-i411.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i412.jpg 1) MoO2(acac)2, H2O2 , Et2O, MgSO4
2) TsOH, CH2Cl2, rt
graphic file with name Beilstein_J_Org_Chem-10-34-i413.jpg i) 59
ii) 95
[405]
graphic file with name Beilstein_J_Org_Chem-10-34-i414.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i415.jpg i) 59
ii) 69
[405]
graphic file with name Beilstein_J_Org_Chem-10-34-i416.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i417.jpg 1) MoO2(acac)2, H2O2, THF, MgSO4
2) 10-camphor-
sulfonic acid, CH2Cl2, rt
graphic file with name Beilstein_J_Org_Chem-10-34-i418.jpg i) 29
ii) 46
[405]
graphic file with name Beilstein_J_Org_Chem-10-34-i419.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i420.jpg 1) H2O2, Et2O,
0 °C, 4 h
2) H2SO4, CH2Cl2, rt, 4 d
graphic file with name Beilstein_J_Org_Chem-10-34-i421.jpg i) 8
ii) 28
[406]
graphic file with name Beilstein_J_Org_Chem-10-34-i422.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i423.jpg 1) MoO2(acac)2, H2O2, Et2O, MgSO4, rt, 22 h
2) TsOH, CH2Cl2, rt, 5 h
graphic file with name Beilstein_J_Org_Chem-10-34-i424.jpg i) 98
ii) 92
[407]
graphic file with name Beilstein_J_Org_Chem-10-34-i425.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i426.jpg 1) MoO2(acac)2, H2O2, Et2O
2) 10-camphor-
sulfonic acid, CH2Cl2
graphic file with name Beilstein_J_Org_Chem-10-34-i427.jpg i) 25
ii) 39
[407]
graphic file with name Beilstein_J_Org_Chem-10-34-i428.jpg graphic file with name Beilstein_J_Org_Chem-10-34-i429.jpg 1) MoO2(acac)2, H2O2 , Et2O, MgSO4
2) BF3·Et2O, CH2Cl2, −78 °C to 0 °C, 5 h
graphic file with name Beilstein_J_Org_Chem-10-34-i430.jpg i) -
ii) 27–35
[175]
[176]