Thermal decomposition of diisopropyl peroxydicarbonate. CIDNP and product studies

Duynstee, E. F. J.; Esser, Michael; Schellekens, R.

doi:10.1016/0014-3057(80)90016-6

Cited by 5 publications

(2 citation statements)

References 3 publications

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“…A thermolysis scheme for diisopropyl peroxydicarbonate was outlined in 1950 2, 6 which, based on the nature of the decomposition products, suggested that the primary step was dissociation into alkoxycarbonyloxyl radicals followed either by decarboxylation or hydrogen atom abstraction from the parent peroxide. This conclusion has been supported by Strong 4 and Duynstee et al 11 Similar conclusions have been drawn from product analysis following the decomposition of dicyclohexyl peroxydicarbonate 8 and of bis(4-tert-butylcyclohexyl) peroxydicarbonate 12 where Scheme 1 the presence of the corresponding alkoxycarbonyloxyl radical and hydrogen atom abstraction of the α-hydrogen atom from the cyclohexane ring of the parent peroxide has been invoked.…”

Section: Introductionsupporting

confidence: 57%

“…Consequently induced decomposition can occur and has been widely reported. [3][4][5]8,10,11 Detailed studies of the species present during the thermolysis of peroxydicarbonates seem rather limited. A thermolysis scheme for diisopropyl peroxydicarbonate was outlined in 1950 2, 6 which, based on the nature of the decomposition products, suggested that the primary step was dissociation into alkoxycarbonyloxyl radicals followed either by decarboxylation or hydrogen atom abstraction from the parent peroxide.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

An EPR spin-trap study of the radicals present during the thermolysis of some novel monoperoxycarbonates and peroxydicarbonates

Mekarbane

Tabner

2000

J. Chem. Soc., Perkin Trans. 2

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EPR spin-trapping experiments have been employed to study the radicals present during the thermolysis of two peroxydicarbonates, bis(4-tert-butylcyclohexyl) peroxydicarbonate (3) and bis(2-ethylhexyl) peroxydicarbonate ( 4), and two monoperoxycarbonates, OO-tert-butyl O-(2-ethylhexyl) monoperoxycarbonate ( 5) and OO-tertbutyl O-isopropyl monoperoxycarbonate (6). The appropriate alkoxycarbonyloxyl radical is trapped during the thermolysis of each of the four peroxides and the tert-butoxyl radical during the thermolysis of 5 and 6. The trapping of a range of second generation carbon-centred radicals is also reported. Evidence is presented that some of these carbon-centred radicals are formed via a 1,5 C to O hydrogen shift whilst others are formed by hydrogen atom abstraction from the parent peroxide.

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