5424-33-9Relevant articles and documents
Photostimulated Reaction of Diphenylarsenide and Diphenylstibide Ions with Haloaromatic Compounds by the SRN1 Mechanism. Electron Transfer vs. Bond Breaking of the Radical Anion Intermediate
Alonso, Ruben A.,Rossi, Roberto A.
, p. 77 - 80 (2007/10/02)
Photostimulated reactions of haloaromatic compounds with potassium diphenylarsenide and potassium diphenylstibide were studied in liquid ammonia. 1-Bromonaphthalene and 9-bromophenanthrene reacted with diphenylarsenide ion to give four products: triphenylarsine, diphenylarylarsine, phenyldiarylarsine, and triarylarsine (aryl = 1-naphthyl and 9-phenanthryl); with 2-chloroquinoline as substrate only the straightforward substitution product 2-qiunolyldiphenylarsine was formed. p-Bromoanisole and 4-chlorobenzophenone reacted with potassium diphenylstibide to give four stibines: triphenylstibine, diphenylarylstibine, phenyldiarylstibine, and triarylstibine (aryl = p-anisyl and 4-benzoylphenyl).These reactions are believed to occur by the SRN1 mechanism with an extra feature of reversible coupling of aryl radicals with arsenide and stibide ions, which causes the scrambling of aryl rings.It is suggested that the low-lying ?* MO of the quinolyl moiety prevents C-As bond breaking of the radical anion intermediate.
