170303-51-2Relevant academic research and scientific papers
Cyclisation of Carbinyl Radicals onto Imines and Hydrazones
Bowman, W. Russel,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
, p. 6369 - 6372 (1994)
The regioselectivity of intramolecular addition of sp3 carbon-centered radicals onto C=N double bonds of imines and hydrazones is influenced by the position and polarisation of the C=N bond.
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2007/10/03)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
Radical cyclisations of imines and hydrazones
Bowman, W. Russell,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
, p. 7959 - 7980 (2007/10/02)
Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.
