51639-37-3Relevant articles and documents
Etude comparative des reactions par transfert monoelectronique entre les germylamines primaires, secondaires et tertiaires et la 3,5-di-tert-butylorthoquinone
Riviere-Baudet, Monique,Morere, Alain,Khallaayoun, Abdelhay
, p. 43 - 49 (2007/10/02)
Several germylamines were treated with 3,5-di-t-butylorthoquinone (1).Competitive 1,2 and 1,4 additions resulted using the tertiary amine Et3GeNPh2.The thermally unstable 1,4 adduct gives 2,2-dialkyl-4,5-(6,8-di-t-butyl)benzo-2-germa-1,3-dioxolanne.The 1,2 adduct leads via intermolecular redistribution to bis(triethylgermyl)oxide ((Et3Ge)2O), and aminal with partial regeneration of the initial quinone.These reations seem to proceed solely via a mono-electron transfer mechanism; the aminyl radical Ph2N and the transitory o-semiquinonic germylated radical formed in the reaction have been characterized by ESR spectroscopy.The o-semiquinonic radical then gives O-germyl-3,5-di-t-butylcatechol by hydrogen abstraction.As ethylene and isobutene have been characterized, these hydrogen abstractions occur from ethyl groups linked to germanium and from t-butyl groups belonging to the organic moieties.In the reaction of the secondary amine Et3GeN(H)Ph, a germylaminyl radical is mainly formed instead of an o-semiquinonic germylated radical, which can explain the lesser amount of germadioxolanne obtained.The quinone 1 is partially transformed in o-diphenol under the action of Mes3GeNH2.No germylated adducts are observed.Aminyl radicals characterized in several reactions between germylamines and 1 were also obtained via monoelectronic transfer between lithium amids and tri-t-butylnitrozobenzene (BNB), thus providing a new, useful method for obtaining such species.
OXIDATIVE ADDITION PRODUCTS IN REACTIONS OF HETEROORGANIC COMPOUNDS WITH SUBSTITUTED o-QUINONES
Razuvaev, G. A.,Abakumov, G. A.,Gladyshev, E. N.,Bayushkin, P. Ya.,Tsaryapkin, V. A.
, p. 1888 - 1893 (2007/10/02)
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