Abstract
Under solvent-free conditions, one-step Beckmann rearrangement of a variety of ketones and aldehydes could proceed in the presence of alumina sulfuric acid (ASA). The ASA reagent can also be used for the preparation of keto- and ald-oximes.
References
1.
(a)
Gowley R.E.
, Org. React. , 1988 , 35 , 1 .
2.
Smith M.B.
, and
March J.
, Advanced Organic Chemistry: Reactions , 5th edn.; John Wiley & Sons, Inc. , New York : 2001 , p. 1415 .
3.
(a)
Beckmann E.
, Chem. Ber. , 1886 , 19 , 988 .
4.
Izumi Y.
,
Sato S.
, and
Urabe K.
, Chem. Lett. , 1983 , 1649 .
5.
(a)
Jung M.E.
, and
Zeng L. M.
Tetrahedron Lett. , 1983 , 24 , 4533 .
6.
Imamato T.
,
Yokoyama H.
, and
Yokoyama M.
, Tetrahedron Lett. , 1981 , 22 , 1803 .
7.
Kamijo T.
,
Harada H.
, and
Lizuka K.
, Chem. Pharm. Bull. , 1984 , 32 , 2560 .
8.
(a)
Pai S.G.
,
Bajpai A. R.
,
Deshpande A. B.
, and
Samant S. D.
, Synth. Commun. , 1997 , 27 , 379 .
9.
Meshram H.M.
, Synth. Commun. , 1990 , 20 , 3253 .
10.
Kath H.
,
Glaser R.
, and
Wietkam J.
, J. Chem. Eng. Technol. , 2001 , 24 , 2 .
11.
Chandrasekhar S.
, and
Gopalaiah K.
, Tetrahedron Lett. , 2003 , 44 , 755 .
12.
Chandrasekhar S.
, and
Gopalaiah K.
, Tetrahedron Lett. , 2002 , 43 , 2455 .
13.
Boruah M.
, and
Konwar D.
, J. Org. Chem. , 2002 , 67 , 7138 .
14.
Luca L. De.
,
Giacomelli G.
, and
Porcheddu A.
, J. Org. Chem. , 2002 , 67 , 6272 .
15.
Wang B.
,
Gu Y.
,
Luo C.
,
Yang T.
,
Yang L.
, and
Suo J.
, Tetrahedron Lett. , 2004 , 45 , 3369 .
16.
Chandrasekhar S.
, and
Gopalaiah K.
, Tetrahedron Lett. , 2003 , 44 , 7437 .
17.
Mao D.
,
Lu G.
, and
Chen Q.
, J. Molec. Catalysis A , 2005 , 240 , 164 .
18.
Li D.
,
Shi F.
,
Guo S.
, and
Deng Y.
, Tetrahedron Lett. , 2005 , 46 , 671 .
19.
Zhang Y.
,
Wang Y.
,
Bu Y.
,
Mi Z.
,
Wu W.
,
Min E.
,
Han S.
, and
Fu S.
, Catal. Commun. , 2005 , 6 , 53 –56
20.
(a)
Ghiaci M.
,
Abbaspur A.
, and
Kalbasi R. J.
, Applied Catalysis A: General , 2005 , 287 , 83 .
21.
Tsuji H.
, and
Setoyama T.
, Chem. Lett. , 2005 , 34 , 1232 .
22.
Guo X.
,
Hou W.
,
Ding W.
,
Fan Y.
,
Yan Q.
, and
Chen Y.
, Microporous and Mesoporous Materials , 2005 , 80 , 269 .
23.
Boero M.
,
Ikeshoji T.
,
Liew C. C.
,
Terakura K.
, and
Parrinello M.
, J. Am. Chem. Soc. , 2004 , 126 , 6280 .
24.
(a)
Gui J.
,
Deng Y.
,
Hu Z.
, and
Sun Z.
, Tetrahedron Lett. , 2004 , 45 , 2681 .
25.
Guo S.
, and
Deng Y.
, Catal. Commun. , 2005 , 3 , 225 –228 ;
26.
Khodaei M.M.
,
Meybodi F. A.
,
Rezai N.
, and
Salehi P.
, Synth. Commun. , 2001 , 31 , 941 .
27.
(a)
Ganboa I.
, and
Palomo C.
, Synth. Commun. , 1983 , 13 , 941 .
28.
Sharghi H.
, and
Hosseini Sarvari M.
, J. Chem. Res.(S) 2001 , 446 .
29.
(a)
Sharghi H.
, and
Hosseini Sarvari M.
, Synthesis , 2002 , 8 , 1057 .
30.
Hosseini Sarvari M.
, and
Sharghi H.
, J. Org. Chem. , 2004 , 69 , 6953 .
31.
Sharghi H.
, and
Hosseini Sarvari M.
, Synlett. , 2001 , 1 , 99 .
32.
Sharghi H.
, and
Hosseini Sarvari M.
, Tetrahedron , 2002 , 58 , 10323 .
33.
Sharghi H.
, and
Hosseini Sarvari M.
, J. Chem. Res.(S) 2003 , 176 .
34.
Hosseini Sarvari M.
, Synthesis , 2005 , 5 , 787 .
35.
Sharghi H.
, and
Hosseini Sarvari M.
, and
Eskandari R.
, J. Chem. Res. , 2005 , 8 , 488 .
36.CRC , Handbook of Tables for Organic Compound Identification , 3rd and 54th edn.
37.
Schofield K.
,
Gregory B. J.
, and
Moodie R. B.
, J. Chem. Soc.(B) , 1970 , 338 .
39.
Brehm L.
, Acta Cryst. , 1972 , B28 , 3646 .
40.
Brady O.L.
, and
Jarrett S. G.
, Acta Cryst. , 1951 , 1227 (Chem. Abs. 45 and 4676 b,c)
