Details

Autor(en) / Beteiligte

• HERBERT C. BROWN

Titel

Free-Radical Reactions of Organoboranes

Ist Teil von

• Boranes in Organic Chemistry, 2019, p.410

Ort / Verlag

Cornell University Press

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Recognition that the organoboranes are excellent sources of free radicals and can participate in free-radical chain reactions came about through detailed mechanistic studies of the reaction of organoboranes with oxygen1–3 (Section XVI-7) and their reaction with α,β-unsaturated carbonyl compounds.⁴ Originally, it was proposed that the autoxidation of a trialkylborane proceeds through an intermediate “borine-peroxide” (19.1).⁵ A similar intermediate was postulated for the peroxide formed in the autoxidation of n-butylboronic anhydride⁶ (19.1). More recently it was recognized that these peroxides are true alkyl peroxide derivatives, containing the structure, ROOB. Thus, the reaction of oxygen with tri-sec-butylborane in dilute solution proceeds