RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2004(14): 2289-2292
DOI: 10.1055/s-2004-831175
DOI: 10.1055/s-2004-831175
PAPER
© Georg Thieme Verlag Stuttgart · New York
4,4′-Bis(dichloroiodo)biphenyl and 3-(Dichloroiodo)benzoic Acid: New Recyclable Hypervalent Iodine Reagents for Vicinal Halomethoxylation of Unsaturated Compounds
Weitere Informationen
Received
12 May 2004
Publikationsdatum:
19. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
19. August 2004 (online)
Abstract
4,4′-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid are convenient recyclable hypervalent iodine reagents for vicinal chloromethoxylation or iodomethoxylation of unsaturated compounds. The reactivity of these reagents in the reaction of vicinal halomethoxylation is generally similar to dichloroiodobenzene and the advantage of their use is that the reduced forms of these reagents can be easily separated from the reaction mixture and reused for the regeneration of the reagents.
Key words
hypervalent iodine - halogens - electrophilic additions - oxidations - alkenes
-
1a
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. -
1b
Hypervalent Iodine Chemistry, Topics in Current Chemistry
Vol. 224:
Wirth T. Springer-Verlag; Berlin / Heidelberg: 2003. -
1c
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
1d
Wirth T.Hirt UH. Synthesis 1999, 1271 -
1e
Skulski L. Molecules 2000, 5: 1331 - 2
Togo H.Sakuratania K. Synlett 2002, 1966 -
3a
Tohma H.Takizawa S.Maegawa T.Kita Y. Angew. Chem. Int. Ed. 2000, 39: 1306 -
3b
Tohma H.Morioka H.Takizawa S.Arisawa M.Kita Y. Tetrahedron 2001, 57: 345 -
3c
Tohma H.Maegawa T.Kita Y. Arkivoc 2003, 62 -
3d
Tohma H.Maegawa T.Kita Y. Synlett 2003, 723 -
3e
Togo H.Nogami G.Yokoyama M. Synlett 1998, 534 -
3f
Togo H.Abe S.Nogami G.Yokoyama M. Bull. Chem. Soc. Jpn. 1999, 72: 2351 -
3g
Togo H.Sakuratania K. Synthesis 2003, 21 -
3h
Abe S.Sakuratania K.Togo H. J. Org. Chem. 2001, 66: 6174 -
3i
Ley SV.Thomas AW.Finch H. J. Chem. Soc., Perkin Trans. 1 1999, 669 -
3j
Ley SV.Schucht O.Thomas AW.Murray PJ. J. Chem. Soc., Perkin Trans. 1 1999, 1251 -
3k
Baxendale IR.Lee A.-L.Ley SV. J. Chem. Soc., Perkin Trans. 1 2002, 1850 -
3l
Baxendale IR.Ley SV.Piutti C. Angew. Chem. Int. Ed. 2002, 41: 2194 -
4a
Yusubov MS.Yusubova RY.Filimonov VD.Chi K.-W. Zh. Org. Chem. 2002, 38: 944 -
4b
Yusubov MS.Yusubova RY.Filimonov VD.Chi K.-W. Synth. Commun. 2004, 34: 443 - 5
Zefirov NS.Sereda GA.Sosonuk SE.Zyk NV.Likhomanova TI. Synthesis 1995, 1359 - 6
Obeid N.Skulski L. Molecules 2001, 6: 869 ; available at URL: http://www.mdpi.org/molecules/papers/61100869.pdf