Amine-promoted nucleophilic addition of tert-butyl hydroperoxide to 2,5-diphenylphosphacymantrene: oxygen-oxygen bond cleavage and novel rearrangement with RO group transfer from oxygen to phosphorus

Peroxyacetals 2a–2j were prepared by TiCl4-promoted nucleophilic addition of both tert-butyl hydroperoxide (TBHP) and an alcohol to the corresponding aldehyde. The reaction works well with a variety of aldehydes, but not with ketones. The magnitude of the equilibrium constant for hemiacetal formation plays an important role; a large constant enables high conversion to peroxyacetal.

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An efficient method for the preparation of tert-butyl esters from benzyl cyanide and tert-butyl hydroperoxide under the metal free condition

RSC Advances ◽

10.1039/c6ra20966a ◽

2016 ◽

Vol 6 (104) ◽

pp. 102023-102027 ◽

Cited By ~ 4

Author(s):

Xiuling Chen ◽

Yan Li ◽

Minghu Wu ◽

Haibing Guo ◽

Longqiang Jiang ◽

...

Keyword(s):

Efficient Method ◽

Bond Cleavage ◽

Bond Formation ◽

One Pot ◽

Free Condition ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Butyl Esters ◽

Tert Butyl Hydroperoxide

A novel protocol to synthesize tert-butyl esters from benzyl cyanides and tert-butyl hydroperoxide has been successfully achieved. Csp3–H bond oxidation, C–CN bond cleavage and C–O bond formation proceeded smoothly in one pot under the metal-free condition.

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Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert-Butyl Hydroperoxide

Synlett ◽

10.1055/s-0036-1588990 ◽

2017 ◽

Vol 28 (12) ◽

pp. 1481-1485 ◽

Cited By ~ 4

Author(s):

Mehdi Adib ◽

Rahim Pashazadeh ◽

Seyed Gohari ◽

Fatemeh Shahsavari

Keyword(s):

Double Bond ◽

Bond Cleavage ◽

Bond Formation ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Tert Butyl Hydroperoxide ◽

New Strategy

A novel tert-butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.

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Metal-Free Csp3–N Bond Cleavage of Amides Using tert-Butyl Hydroperoxide as Oxidant

Synlett ◽

10.1055/s-0034-1379879 ◽

2015 ◽

Vol 26 (04) ◽

pp. 543-546 ◽

Cited By ~ 6

Author(s):

Hu Cai ◽

Shengmei Guo ◽

Zheng Zhu ◽

Lin Lu ◽

Wenbiao Zhang ◽

...

Keyword(s):

Bond Cleavage ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Tert Butyl Hydroperoxide

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A mechanism of mitochondrial damage induced by tert-butyl hydroperoxide and microsomes in vitro

Physiologia Plantarum ◽

10.1034/j.1399-3054.1990.800210.x ◽

1990 ◽

Vol 80 (2) ◽

pp. 226-232

Author(s):

Tomoaki Matsuo ◽

Yumiko Kashiwaki ◽

Saburo Itoo

Keyword(s):

Mitochondrial Damage ◽

Butyl Hydroperoxide ◽

Tert Butyl ◽

Tert Butyl Hydroperoxide

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Oxygen-Oxygen Bond Cleavage and Formation in Co(II) Mediated Stoichiometric O2 Reduction via the Potential Intermediacy of a Co(IV) Oxyl Radical

10.26434/chemrxiv.7176392 ◽

2018 ◽

Author(s):

Lucie Nurdin ◽

Denis M. Spasyuk ◽

Laura Fairburn ◽

Warren Piers ◽

Laurent Maron

Keyword(s):

Bond Cleavage ◽

Peroxo Complex ◽

Oxygen Oxygen ◽

O2 Reduction ◽

Oxygen Bond ◽

Pentadentate Ligand

Diprotonation of a remarkably stable, toluene soluble cobalt peroxo complex supported by a neutral, dianionic pentadentate ligand leads to facile O-O bond cleavage and production of a highly reactive Co(IV) oxyl cation intermediate that dimerizes and releases O2. These processes are relevant to both O2 reduction and O2 evolution and the mechanism was probed in detail both experimentally and computationally.

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