Journal of Organometallic Chemistry p. 333 - 340 (1970)
Update date:2022-08-04
Topics:
Wiberg, Nils
Joo, Wan-Chul
Phenylmagnesium bromide reacts with triphenylsilyl azide (in contrast to organyl azides) in two parallel reactions. One type of reaction is the substitution of the azide group by the magnesium-bound organyl residue. The other is the formation of the adduct, (C6H5)3SiN3·C6H5MgBr, containing an N-diazonium group. At higher temperatures the adduct decomposes by elimination of N2 to give (C6H5)3SiN(C6H5)MgBr. The same type of reaction generally occurs when silyl azicles R3SiN3 react with arylmagnesium halides R′MgHal. The hydrolysis of the silyl amide leads to amines R′NH2. In connection with this the formation of R3SiNR′(MgHal) by the reaction of R3SiN3 with R′MgHal (=R′Hal + Mg) provides a simple procedure to prepare aromatic amines from aromatic halides.
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Doi:10.1081/SCC-100105117
(2001)Doi:10.1021/ja983716r
(2000)Doi:10.1021/jacs.6b02470
(2016)Doi:10.1002/ejoc.201500361
(2015)Doi:10.1039/c29700000484
(1970)Doi:10.1007/BF00949630
(1980)
