Abstract
A novel method was developed to synthesise azoarenes from nitrosobenzenes under mild conditions. Samarium (II) iodine was used to achieve the N–N coupling. The method also provides evidence for the proposed mechanism involved in the reduction of nitro compounds to the amines with SmI2.
Keywords
References
1.
Girard P.
,
Namy J. L.
, and
Kagan H. B.
, J. Am. Chem. Soc. , 1980 , 102 , 2693 .
2.
Petr Z.
, and
Bhavdeep S.
, Chem. Rev. , 1994 , 94 , 1621 .
3.
Kagan H.B.
, Tetrahedron , 2003 , 59 , 10351 .
4.
Alain K.
, and
Anne-Marie L.
, Chem. Rev. , 1999 , 99 , 745 .
5.
Feuer H.
,
Bartlett R. S.
,
Vincent B. F.
, and
Anderson R. S.
, J. Org. Chem. , 1965 , 30 , 2880 .
6.
Olah G.A.
, J. Am. Chem. Soc. , 1959 , 81 , 3165 .
7.
Hutchins R.O.
,
Lamson D. W.
,
Rua L.
,
Milewski C.
, and
Maryanoff B.
, J. Org. Chem. , 1971 , 36 , 803 .
8.
Ohe K.
,
Uemura S.
,
Sugita N.
,
Masuda H.
, and
Taga T.
, J. Org. Chem. , 1989 , 54 , 4169 .
9.
Kim B.H.
,
Kim S. K.
,
Lee Y. S.
,
Jun Y. M.
,
Baik W.
, and
Lee B. M.
, Tetrahedron Lett. , 1997 , 38 , 8303 .
10.
Brady E.D.
,
Clark D. L.
,
Keogh D. W.
,
Scott B. L.
, and
Watkin J. G.
, J. Am. Chem. Soc. , 2002 , 124 , 7007 .
11.
Defoin A.
, Synthesis , 2004 , 5 , 706 .
12.
Saeid F.
, Acta Chim. Slov. , 2007 , 54 , 647 .
13.
Nanjundaswamy H.M.
, J. Chem. Res. (S) , 2005 , 12 , 772 .
14.
Hanson P.
,
Taylor A. B.
,
Walton P. H.
, and
Timms A. W.
, Org. Biomol. Chem. , 2007 , 5 , 679 .
15.
Nallaiah C.
, and
Strickson J. A.
, Tetrahedron , 1986 , 42 , 4083 .
16.
Furin G.G.
, J. Fluorine Chem. , 1985 , 28 , 1 .