13732-86-0Relevant articles and documents
Directed ortho-metalation, a new insight into organosodium chemistry
Gissot, Arnaud,Becht, Jean-Michel,Desmurs, Jean Roger,Pevere, Virginie,Wagner, Alain,Mioskowski, Charles
, p. 340 - 343 (2002)
Finely dispersed metallic sodium in combination with an alkyl chloride RCcan replace organolithium reagents in the ortho-metalation of aromatic compounds (see scheme). The in situ generated base is consumed as soon as it is formed, which avoids Wurtz coupling, the usual side reaction, and the handling and storage of highly reactive alkyl sodium bases. Reaction conditions are mild, the reaction is easy to scale up, and the reagents needed are inexpensive.
Synthesis of Substituted Dibenzophospholes. Part 2. Syntheses of Intermediate Biphenyls and Quaterphenyls
Cornforth, John,Sierakowski, Andrew F.,Wallace Timothy W.
, p. 2299 - 2316 (2007/10/02)
A general procedure for synthesis of 4",6'-dialkoxy-2',2"-diamino-m-quaterphenyls has been established.Copper(I) t-butoxide is used to prepare 2,6-dinitrophenyls from 1,3-dinitrobenzene and aryl iodides.One of the nitro-groups is then exchanged for a methoxy-group by sodium methoxide in hexamethylohosphoramide; the resulting 2-methoxy-6-nitrobiphenyls are then iodinated in the 5-position.Ullmann coupling then gives the dinitroquaterphenyls which are reduced to the diamines.An alternative route from 2,2',4,4'-tetranitrobiphenyl was explored; arylation was easy but alkoxydenitration was indiscriminate.Some 71 new derivatives of biphenyl, terphenyl, and quterphenyl are reported.
