Elsevier

Tetrahedron Letters

Volume 35, Issue 44, 31 October 1994, Pages 8197-8200
Tetrahedron Letters

Ultrasonic reaction of triarylbismuthines and triarylstibines with iodosylbenzene. Mild oxidizing ability of the organobismuth oxide function for organic substrates

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Abstract

Reaction of triarylbismuthines 1 with iodosylbenzene in dichloromethane under ultrasonic irradiation leads to the generation of triarylbismuthine oxides 2 as a bright yellow solution, in which activated alcohols are easily oxidized to carbonyl compounds, triphenylphosphine is converted into oxide and hydrazobenzene is rapidly dehydrogenated to azobenzene. Triphenylstibine 8 is similarly oxidized to give stibine oxide 9, which lacks the corresponding oxidizing ability.

Sonochemical reaction of triarylbismuthines and triarylstibines with iodosylbenzene produces the corresponding oxides.

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