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. 2016 Aug 3;12:1647–1748. doi: 10.3762/bjoc.12.162

Table 23.

Base-catalyzed intramolecular rearrangement of 1,2-dioxetanes.

graphic file with name Beilstein_J_Org_Chem-12-1647-i150.jpg

Entry X R Ar-OH Reaction conditions Ref.

1 O t-Bu Inline graphic
R1, R2 = H, OMe, CO2Me, CO2H, CH2OH
TBAF in DMSO at 25 °C for 1 h [463]
2 O t-Bu Inline graphic
R = H, OMe; Y = O, S
NaOH in СH3CN/H2O at 45 °C [464]
3 O t-Bu graphic file with name Beilstein_J_Org_Chem-12-1647-i153.jpg TBAF in DMSO (NMP or DMF) at 45–100 °C [465]
4 O Me, Et, iPr, iBu in NMP at 50–100 °C or in TBAF/NMP at 35–60 °C [466]
5 O t-Bu graphic file with name Beilstein_J_Org_Chem-12-1647-i154.jpg TBAF in CH3CN at 45 °C [467]
6 NBoc t-Bu 3-OH-C6H4
3-OMe-C6H4
6-OH-C10H6
TBAF in DMSO at 25 °C [468469,473]
7 S, SO, S(O)2 t-Bu 3-OH-C6H4
3-OMe-C6H4
3-OAc-C6H4
TBAF in DMSO at 25 °C [472]
8 O t-Bu HO-phenanthrenyl TBAF in CH3CN at 45 °C [474]
9 O t-Bu Inline graphic
R = H, Me, Ph
TBAF in CH3CN or NaOH in H2O at 45 °C [475]
10 graphic file with name Beilstein_J_Org_Chem-12-1647-i156.jpg TBAF in DMSO at 25 °C [470]
11 graphic file with name Beilstein_J_Org_Chem-12-1647-i157.jpg TBAF in THF/DMSO (1:1) at 25 °C [476]
12 graphic file with name Beilstein_J_Org_Chem-12-1647-i158.jpg DBU in CH3CN at 25 °C [477]
13 graphic file with name Beilstein_J_Org_Chem-12-1647-i159.jpg TBAF in DMSO/PBS buffer [471]