Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• Abstract Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate

Photosonochemical catalytic ring opening of α-epoxyketones

• Hamid R. Memarian and
• Ali Saffar-Teluri

Beilstein J. Org. Chem. 2007, 3, No. 2, doi:10.1186/1860-5397-3-2

• -epoxyketones in the presence of various nucleophiles has received considerable attention in recent years, partially owing to current interest in single electron transfer (SET) process and also because of potential application in organic synthesis. Such reactions have been recognized as important processes not

• only in thermal but also in photochemical transformations. Single electron transfer (SET) induced ring opening reactions of epoxides and α-epoxyketones have demonstrated C-C and C-O bond cleavages through photo-induced electron transfer by various electron donors such as triethylamine (TEA), [21

• ] tribenzylamine (TBA) [20] and 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) [22][23][24] or thermally induced single electron transfer by electron donating compounds such as samarium diiodide, [25] tributyltin hydride [26] and bis(cyclopentadienyl)titanium(III) chloride. [27] Ring opening reactions of epoxides