Abstract
The bromination of camphor has been carried out on a multi-gram scale by a mixture of KBr and KBrO3 in the presence of acid or with HBr/NaBr - H+ and H2O2/oxone® as the oxidant. The 3-bromocamphor is then efficiently converted to camphorquinone by an improved oxidation protocol using DMSO and sodium carbonate of tetrabutyl ammonium iodide.
References
1.
Clark J.
, and
Macquarrie D.
, eds, Handbook of green chemistry and technology , Blackwell Science ; Oxford , 2002 .
2.
Anastas P.T.
, and
Williamson T.C.
, Green chemistry, ACS Symposium Series 626 , American Chemical Society , Washington DC , 1996 .
3.
Podgoršek A.
,
Stavber S.
,
Zupan M.
, and
Iskra J.
, Green Chem. , 2007 , 9 , 1212 .
4.
Eissen M.
, and
Lenoir D.
, Chem.-Eur. J. , 2008 , 14 , 9830 .
5.
Podgoršek A.
,
Zupan M.
, and
Iskra J.
, Angew. Chem., Int. Ed. , 2009 , 48 , 8424 .
6.
Ho T.-L.
,
Balaram Gupta B.G.
, and
Olah G.A.
, Synthesis , 1977 , 676 .
7.
Barhate N.B.
,
Garjare A.S.
,
Wakharkar R.D.
, and
Bedekar A.V.
, Tetrahedron , 1999 , 55 , 11127 .
8.
Vyas P.V.
,
Bhatt A.K.
,
Ramachandraiah G.
, and
Bedekar A.V.
, Tetrahedron Lett. , 2003 , 44 , 4085 .
9.
Dieter R.K.
,
Nice L.E.
, and
Velu S.E.
, Tetrahedron Lett. , 1996 , 37 , 2377 .
10.
Tamhankar B.V.
,
Desai U.V.
,
Mane R.B.
,
Wadgaonkar P.P.
, and
Bedekar A.V.
, Synth. Commun. , 2001 , 31 , 2021 .
11.
Nair V.
,
Panicker S.B.
,
Augstine A.
,
George T.G.
,
Thomas S.
, and
Vairamani M.
, Tetrahedron , 2001 , 57 , 7417 .
12.
Dewkar K.G.
,
Narina V.S.
, and
Sudalai A.
, Org. Lett. , 2003 , 5 , 4501 .
13.
Muathen H.A.
, Synth. Commun. , 2004 , 34 , 3545 .
14.
Ye C.
, and
Shreeve M.J.
, J. Org. Chem. , 2004 , 69 , 8561 .
15.
Butler A.
, Current Opin. Chem. Biol. , 1998 , 2 , 279 .
16.
Kikushima K.
,
Moriuchi T.
, and
Hirao T.
, Tetrahedron , 2010 , 66 , 6909 .
17.
Tillu V.H.
,
Shinde P.D.
,
Bedekar A.V.
, and
Wakharkar R.D.
, Synth. Commun. , 2003 , 33 , 1399 .
18.
Pravst I.
,
Zupan M.
, and
Stavber S.
, Tetrahedron Lett. , 2006 , 47 , 4707 .
19.
Meshram H.M.
,
Reddy P.N.
,
Vishnu P.
,
Sadashiv K.
, and
Yadav J.S.
, Tetrahedron Lett. , 2006 , 47 , 991 .
20.
Woodward R.B.
, Pure Appl. Chem. , 1973 , 33 , 145 .
21.
Meinwald J.
, and
Klingele H.O.
, J. Am. Chem. Soc. , 1966 , 88 , 2071 .
22.
Carter K.N.
, J. Org. Chem. , 1966 , 31 , 4257 .
23.
Li Q.
,
Yang S.-B.
,
Zhang Z.
,
Li L.
, and
Xu P.-F.
, J. Org. Chem. , 2009 , 74 , 1627 .
24.
Oppolzer W.
, Tetrahedron , 1987 , 43 , 1969 .
25.
Kipping S.
, and
Pope W.J.
, J. Chem. Soc. , 1893 , 63 , 548 .
26.
Adimurthy S.
,
Ramachandraiah G.
,
Bedekar A.V.
,
Ghosh S.
,
Ranu B.C.
, and
Ghosh P.K.
, Green Chem. , 2006 , 8 , 916 .
27.
Adimurthy S.
,
Ghosh S.
,
Patoliya P.U.
,
Ramachandraiah G.
,
Agrawal M.
,
Ghandhi M.R.
,
Upadhyay S.C.
,
Ghosh P.K.
, and
Ranu B.C.
, Green. Chem. , 2008 , 10 , 232 .
28.
White J.D.
,
Wardrop D.J.
, and
Sundermann K.F.
, Org. Synth. Coll. , 2004 , 10 , 204 .
29.
Hattori K.
,
Yoshida T.
,
Rikuta K.-I.
, and
Miyakoshi T.
, Chem. Lett. , 1994 , 1885 .