Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2003(5): 0702-0704
DOI: 10.1055/s-2003-38379
DOI: 10.1055/s-2003-38379
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York
Environmentally-Friendly Wohl-Ziegler Bromination: Ionic-Liquid Reaction and Solvent-Free Reaction
Further Information
Received
28 December 2002
Publication Date:
28 March 2003 (online)
Publication History
Publication Date:
28 March 2003 (online)

Abstract
Environmentally-friendly Wohl-Ziegler bromination of benzylic methyl groups was successfully carried out in ionic-liquid and solvent-free systems, to produce the corresponding benzylic bromides in good to moderate yields.
Key words
Wohl-Ziegler bromination - benzylic bromide - N-bromosuccinimide (NBS) - 2,2′-azobis(isobutyronitrile) (AIBN) - benzoyl peroxide - ionic-liquid - solvent-free
-
1a
March J. In Advanced Organic Chemistry 4th Ed.: Willey & Sons; New York: 1992. Chap. 14. and references are cited therein -
1b
Dauben HJ.McCoy LL. J. Am. Chem. Soc. 1959, 81: 4863 -
1c
Walling C.Rieger AL.Tanner DD. J. Am. Chem. Soc. 1963, 85: 3129 -
1d
Greenwood FL.Kellert MD.Sedlak J. Org. Synth., Coll. Vol. 4 1963, 108 -
1e
Campaigne E.Tullar BF. Org. Synth., Col. Vol. 4 1963, 921 -
1f
Cram DJ.Helgeson RC. J. Am. Chem. Soc. 1966, 88: 3515 - Recent reports:
-
2a
Hartman G.Halczenko W.Phillips BT. J. Org. Chem. 1986, 51: 142 -
2b
Stevens CV.Heecke GV.Barbero C.Patora K.De Kimpe N.Verhe R. Synlett 2002, 1089 -
2c
Ojida A.Park S.-K.Mito-oka Y.Hamachi I. Tetrahedron Lett. 2002, 43: 6193 -
2d
Sygula A.Karlen SD.Sygula R.Rabideau PW. Org. Lett. 2002, 4: 3135 -
2e
Ma S.Ni B. J. Org. Chem. 2002, 67: 8280 -
2f
Mehta G.Sarma PVVS. Tetrahedron Lett. 2002, 43: 9343 - Review:
-
3a
Loupy A.Petit A.Hamelin J.Texier-Boullet F.Jacquault P.Mathe D. Synthesis 1998, 1213 -
3b Recent report:
Sharghi H.Hosseini M. Synthesis 2002, 1057 -
3c
Melucci M.Barbarella B.Sotgiu G. J. Org. Chem. 2002, 67: 8877 - Reviews:
-
4a
Welton T. Chem. Rev. 1999, 99: 2071 -
4b
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
4c
Sheldon R. Chem. Commun. 2001, 2399 -
4d
Sheldon RA. Pure Appl. Chem. 2000, 72: 1233 -
5a Recent
reports selected:
Ren RX.Zueva LD.Ou W. Tetrahedron Lett. 2001, 42: 8441 -
5b
Morrison DW.Forbes DC.Davis JH. Tetrahedron Lett. 2001, 42: 6053 -
5c
Mayo KG.Nearhoof EH.Kiddle JJ. Org. Lett. 2002, 4: 1567 -
5d
Yanada R.Takemoto Y. Tetrahedron Lett. 2002, 43: 6849 -
5e
Ansari IA.Gree R. Org. Lett. 2002, 4: 1507 -
5f
Fukuyama T.Shinmen M.Nishitani S.Sato M.Ryu I. Org. Lett. 2002, 4: 1691 -
5g
Xie Y.-Y.Chen Z.-C.Zheng Q.-G. Synthesis 2002, 1505 -
6a
Yamazaki O.Togo H.Matsubayashi S.Yokoyama M. Tetrahedron 1999, 55: 3735 -
6b
Yamazaki O.Yamaguchi K.Yokoyama M.Togo H. J. Org. Chem. 2000, 65: 5440 -
6c
Togo H.Matsubayashi S.Yamazaki O.Yokoyama M. J. Org. Chem. 2000, 65: 2816 -
6d
Yamazaki O.Togo H.Yokoyama M. J. Chem. Soc., Perkin Trans 1. 1999, 2891 -
6e
Atsushi R.Togo H. Tetrahedron 2001, 57: 5915 -
6f
Sugi M.Togo H. Tetrahedron 2002, 58: 3171 -
7a Co(I)-mediated
living radical polymerization:
Carmichael AJ.Haddleton DM.Bon SAF.Seddon KR. Chem. Commun. 2000, 1237 -
7b Triethylborane-induced
radical cyclizations with Bu3SnH:
Yorimitsu H.Oshima K. Bull. Chem. Soc. Jpn. 2002, 75: 853 -
8a
Chapman NB.Williams JFA. J. Chem. Soc. 1952, 5044 -
8b
Mitchell RH.Lai Y.-H.Williams RV. J. Org. Chem. 1979, 44: 4733