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Functionalization of substrates using unsaturated organic peroxides

In organic synthesis, radical reactions are commonly used for chain reactions (Giese, 1986).  Radicals are used as synthetic intermediates in reactions which are often difficult to accomplish by other means and which can selectively occur under very mild conditions.  The protection of functional groups, often essential for synthtic sequences of ionic reactions, is mostly not required for radical reactions (Curran e.a., 1996).

Organic peroxides are well established synthetic agents as source for radicals in the manufacture of many pharmaceutical intermediates, herbicides, insecticides and various other fine chemicals.  Using appropriate conditions for storage and handling of organic peroxides, potential hazards of run-away situations can be excluded and reactions are controlled and can be intrinsically safe (Akzo Nobel PC Product Catalogue; Swern, 170; Houben-Weyl, 1988).

Because of the specific nature of radical chemical reactions, organic peroxides offer opportunities to reduce the number of reaction steps in synthetic routes, which would be needed applying classical synthetic procedures.  In particular, introduction of functional groups can be achieved by using special organic peroxides.

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Organic Peroxides in Radical Synthesis Reactions

Peroxides and Azo-compounds available at Acros Organics:

10515 2,2'-azobis(2-methylpropionitrile), 98%
17014 tert-butyl peroxybenzoate, 98%
18034 tert-butyl hydroperoxide, 70% solution in water
21178 benzoyl peroxide, 75% remainder water
34974 lauroyl peroxide, 99%
34975 2,2'-azobis(2-methylbutyronitrile), 98%
34977 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 75% solution in aromatic free mineral spirit
34980 1,1-di(tert-butylperoxy)cyclohexane, 50% solution in aromatic free mineral spirit
34981 tert-butyl peroxy-3,5,5-trimethylhexanoate, 97%
34983 2,2-di(tert-butylperoxy)butane, 50% solution in aromatic free mineral spirit
34984 tert-butylperoxy isopropyl carbonate, 75% solution in aromatic free mineral spirit
34985 tert-butylperoxy 2-ethylhexyl carbonate, 95%
34986 tert-butyl peroxyacetate, 50% solution in aromatic free mineral spirit
34988 dicumyl peroxide, 99%
34989 di(tert-butylperoxyisopropyl)benzene, 96%
34990 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 92%
34991 tert-butyl cumyl peroxide, 94%
34993 di-tert-butyl peroxide, 99%
34994 3,6,9-triethyl-3,6,9-trimethyl-1,4,7-triperoxynonane, 41% solution in aromatic free mineral spirit
34996 cumyl hydroperoxide, 80%
34997 3,4-dimethyl-3,4-diphenylhexane, 98%
34998 2,3-dimethyl-2,3-diphenylbutane, 95%
37855 tert-butylperoxy allyl carbonate, 70 wt.% solution in odourless mineral spirit
37856 allyl cumyl peroxide, 70-80 wt.% solution in 2-phenylisopropanol
37857 tert-butyl monoperoxymaleate, 25 wt.% paste in dibutyl maleate
37858 2,4,6-tris(t-butylperoxy)-1,3,5-triazine, 35 wt.% in toluene/bis(2-ethylhexyl)adipate
37859 2,2-di(4,4-di(tert-butylperoxy)cyclohexyl)propane, 20 wt.% solution in ethylbenzene