Abstract
Mg(NO3)2.6H2O was an efficient nitrating agent in the presence of a mixture of AI2O3/MeSO3H (AMA) as a novel heterogeneous system for the nitration of aromatic compounds without use of any organic solvents and with high selectivity. The reaction proceeds at room temperature for the nitration of highly reactive aromatic compounds such as phenols and anilines.
References
1.
Esakkidurai T.
, and
Pitchumani K.J.
, Mol. Catal. A: Chem. , 2002 , 185 , 305 .
2.
Samajdar S.
,
Becker F.F.
, and
Banik B.K.
, Tetrahedron Lett. , 2000 , 41 , 8017 .
3.
Botvay A.
,
Mathe A.
, and
Poppl L.
, Polymer , 1999 , 40 , 4965 .
4.
Tasneem A.M.M.
,
Rajanna K.C.
, and
Saiparakash P.K.
, Synth. Commun. , 2001 , 31 , 1123 .
5.
Ono N.
, The nitro group in organic synthesis , Wiley-VCH , Weinheim , 2001 .
6.
Olah G.A.
,
Malhotra R.
, and
Narang S.C.
, Nitration: methods and mechanisms , Wiley-VCH , Weinheim , 1989 .
7.
Coombes R.G.
, Comprehensive organic chemistry ,
Sutherland I.O.
(ed.) VCH , New York , 1990 .
8.
Olah G.A.
, and
Kuhn S.J.
, J. Am. Chem. Soc. , 1962 , 84 , 3684 .
9.
Peng X.
,
Suzuki H.
, and
Lu C.
, Tetrahedron Lett. , 2001 , 42 , 4357 .
10.
Bak R.R.
, and
Smallridge A.J.
, Tetrahedron Lett. , 2001 , 42 , 6767 .
11.
Iranpoor N.
,
Firouzabadi H.
, and
Heydari R.
, Synth. Commun. , 2003 , 33 , 703 .
12.
Ramana M.M.V.
,
Malik S.S.
, and
Parihar J.A.
, Tetrahedron Lett. , 2004 , 45 , 8681 .
13.
Strazzolini P.
,
Giumanini A.G.
, and
Runcio A.
, Tetrahedron Lett. , 2001 , 42 , 1387 .
14.
Bozell J.J.
, and
Hoberg J.O.
, Tetrahedron Lett. , 1988 , 39 , 2261 .
15.
Bahulayan D.
,
Narayan G.
,
Sreekumar V.
, and
Lalithambika M.
, Synth. Commun. , 2002 , 32 , 3565 .
16.
Olah G.A.
,
Krishnamurthy V.V.
, and
Narang S.C.
, J. Org. Chem. , 1982 , 47 , 596 .
17.
Cornelis A.
, and
Laszlo P.
, Synthesis , 1985 , 909 .
18.
Mellor J.M.
,
Mittoo S.
,
Parkes R.
, and
Millar R.W.
, Tetrahedron , 2000 , 56 , 8019 .
19.
Hajipour A.R.
, and
Ruoho A.E.
Tetrahedron Lett. , 2005 , 8307 .
20.
Zhang P.
,
Cedilote M.
,
Cleary T.P.
, and
Pierce M.E.
, Tetrahedron Lett. , 2007 , 48 , 8659 .
21.
Riego J.M.
,
Sedin Z.
,
Zaldivar J.M.
,
Marziano N.C.
, and
Tortato C.
, Tetrahedron Lett. , 1996 , 37 , 513 .
22.
Zolfigol M.A.
,
Ghasemi E.
, and
Madrakian E.
, Synlett , 2003 , 191 .
23.
Zolfigol M.A.
,
Madrakian E.
, and
Ghasemi E.
, Molecules , 2002 , 7 , 734 .
24.
Yin W.-P.
, and
Shi M.
, J. Chem. Res. , 2006 , 549 .
25.
Sun H.-B.
,
Hua R.
, and
Yin Y.
, J. Org. Chem. , 2005 , 70 , 9071 .
26.
Olah G.A.
,
Reddy V.
, and
Prakash S.
, Synthesis , 1992 , 1087 .
27.
Bosnich B.
,
Nyholm R.S.
,
Pauling P.J.
, and
Tobe M.L.
, J. Am. Chem. Soc. , 1968 , 90 , 4742 .
28.
Nonoyama N.
,
Chiba K.
,
Hisatome K.
,
Suzuki H.
, and
Shintani F.
, Tetrahedron Lett. , 1999 , 40 , 6933 .
29.
Rodrigues J.A.R.
,
Filho A.P.D.O.
,
Moran P.J.S.
, and
Custodio R.
, Tetrahedron , 1999 , 55 , 6733 .
30.
Kimura M.
,
Kajita K.
,
Naoyuki O.
, and
Morosawa S.
, J. Org. Chem. , 1990 , 55 , 4887 .
31.
Frost C.G.
,
Hartley J.P.
, and
Griffin D.
, Tetrahedron Lett. , 2002 , 43 , 4789 .
32.
Parac-Vogt T.N.
, and
Binnemans K.
, Tetrahedron Lett. , 2004 , 45 , 3137 .
33.
Rajagopal R.
, and
Srinivasan K.V.
, Ultrason. Sonochem. , 2003 , 10 , 41 .
34.
Sharghi H.
, and
Kaboudin B.
, J. Chem. Res. (S) , 1998 , 628 .
35.
Sharghi H.
, and
Hosseini Sarvari M.
, J. Chem. Res.(S) , 2001 , 446 .
36.
Sharghi H.
, and
Hosseini Sarvari M.
, Synth. Commun. , 2003 , 33 , 205 .
37.
Sharghi H.
, and
Hosseini Sarvari M.
, Tetrahedron , 2003 , 59 , 3627 .
38.
Sharghi H.
, and
Hosseini Sarvari M.
, J. Org. Chem. , 2003 , 68 , 4096 .
39.
Sharghi H.
, and
Hosseini Sarvari M.
, Synthesis , 2003 , 6 , 879 .
40.
Sharghi H.
, and
Jokar M.
, Heterocycles , 2007 , 71 , 2721 .
41.
Hosseini-Sarvari M.
, and
Tavakolian M.
, J. Chem. Res. , 2008 , 318 .
42.Vogel's Text book of practical organic chemistry , 4th edn, Longman , London & New York , 1986 .
43.
Bose A.K.
,
Ganguly S.N.
,
Manhas M.S.
,
Rao S.
,
Speck J.
,
Pekelny U.
, and
Pombo-Villars E.
, Tetrahedron Lett. , 2006 , 47 , 1885 .
