Abstract
Raney Ni–AI alloy in a dilute aqueous alkaline solution has been shown to be a powerful reducing agent and is highly effective for the reduction of alkylbenzils and alkoxybenzils to afford the corresponding 1,2-diarylethers at 90°C, in the absence of organic solvents. 4,4′-Dinitrobenzil was transformed selectively to 1,2-bis(4-aminophenyl)-ethane.
References
1.
Pearl I.A.
, and
Dehn W. M.
, J. Am. Chem. Soc. , 1938 , 60 , 57 .
2.
Vedejs E.
, Org. React. , 1975 , 22 , 401 .
3.
Szmant H.H.
, and
Harmuth C. M.
, J. Am. Chem. Soc. , 1964 , 86 , 2909 .
4.
Heilmann S.M.
,
Rasmussen J. K.
, and
Smith H. K.
II
, J. Org. Chem. , 1983 , 48 , 987 .
5.
Jenkins S.S.
,
Buck J. S.
, and
Bigelow L. A.
, J. Am. Chem. Soc. , 1930 , 52 , 4495 .
6.
Murata K.
,
Okano K.
,
Miyagi M.
,
Iwane H.
,
Noyori R.
, and
Ikariya T.
, Org. Lett. , 1999 , 1 , 1119 .
7.
Abu-Reziq R.
,
Avnir D.
, and
Blum J.
, J. Mol. Cat. A: Chem. , 2002 . 187 , 277 .
8.
Stapelfeldt H.E.
, and
Perone S. P.
, Anal. Chem. , 1969 , 41 , 623 .
9.
Buisson D.
,
Baba S. E.
, and
Azerad R.
, Tetrahedron Lett. , 1986 , 27 , 4453 .
10.
Papa D.
,
Schwenk E.
, and
Whitman B.
, J. Org. Chem. , 1942 , 7 , 587 .
11.
Liu G.-B.
,
Dai L.
,
Gao X.
,
Li M.-K.
, and
Thiemann T.
, Green Chem. , 2006 , 8 , 781 .
12.
Porter N.A.
,
Wu W.-X.
, and
McPhail A. T.
, Tetrahedron Lett. , 1991 , 32 , 707 .
13.
Tashiro M.
,
Yamato T.
, and
Fukuta G.
, J. Org. Chem. , 1978 , 43 , 1413 .
14.
Huang M.
, J. Am. Chem. Soc. , 1948 , 70 , 2802 .
15.
Serijan K.T.
, and
Wise P. H.
, J. Am. Chem. Soc. , 1951 , 73 , 4766 .
16.
Serijan K.T.
, and
Wise P. H.
, J. Am. Chem. Soc. , 1952 , 74 , 365 .
17.
Serijan K.T.
, and
Wise P. H.
, J. Am. Chem. Soc. , 1951 , 73 , 5191 .
18.
Zhou J.
, and
Fu G. C.
, J. Am. Chem. Soc. , 2003 , 125 , 14726 .
19.
Zhou J.
, and
Fu G. C.
, J. Am. Chem. Soc. , 2003 , 125 , 12527 .
