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Synthesis 2005(5): 705-707
DOI: 10.1055/s-2005-861809
DOI: 10.1055/s-2005-861809
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Electrochemical Oxidation of Benzoins to Benzils in the Presence of a Catalytic Amount of KI in Basic Media
Further Information
Received
27 September 2004
Publication Date:
14 February 2005 (online)
Publication History
Publication Date:
14 February 2005 (online)
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Abstract
Various benzoins were transformed into the corresponding benzils via an electrochemical method. Although the strategy of oxidizing benzoins to the corresponding benzils is generally chosen depending on the nature of the aromatic moiety, the electrochemical technique reported herein allows oxidation that is widely applicable, and without the use of environmentally undesirable oxidants.
Key words
alcohols - ketones - dehydrogenations - iodine - electron transfer
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1a
Vollhardt KPC.Schore NE. Organic Chemistry 2nd ed.: Freeman; New York: 1994. p.924-929 -
1b
Smith LI.Hoehn HH. Org. Synth., Coll. Vol. III Wiley; New York: 1955. p.356 -
1c
Johnson JR.Grummitt O. Org. Synth., Coll. Vol. III Wiley; New York: 1955. p.806 -
1d
Cope AC.Smith DS.Cotter RJ. Org. Synth., Coll. Vol. IV Wiley; New York: 1963. p.377 -
1e
Vofsi D.Asscher M. Org. Synth., Coll. Vol. V Wiley; New York: 1973. p.1076 -
1f
Morrison H.Danishefsky S.Yates P. J. Org. Chem. 1961, 26: 2617 - 2
Weiss M.Apple M. J. Am. Chem. Soc. 1948, 70: 3666 - 3
Clarke HT.Dreger EE. Org. Synth., Coll. Vol. I Wiley; New York: 1941. p.87 - 4
Cainelli G.Cardillo G. Chromium Oxidants in Organic Chemistry Springer; Berlin: 1984. -
5a
Iranpoor N.Firouzabadi H.Zolfigol MA. Bull. Chem. Soc. Jpn. 1998, 71: 905 -
5b
Tymonko SA.Nattier BA.Mohan RS. Tetrahedron Lett. 1999, 40: 7657 -
5c
Sharma VB.Jain SL.Sain B. Tetrahedron Lett. 2003, 44: 383 -
5d
Firouzabadi H.Mohammadpour-Baltork I. Bull. Chem. Soc. Jpn. 1992, 65: 1131 -
5e
Mahjoub AR.Ghammami S.Kassaee MZ. Tetrahedron Lett. 2003, 44: 4555 -
5f
Firouzabadi H.Iranpoor N.Amani K. Synthesis 2003, 408 -
5g
Bhar S.Chaudhuri SK. Tetrahedron 2003, 59: 3493 -
5h
Mitsumoto Y.Nitta M. Bull. Chem. Soc. Jpn. 2003, 76: 1029 -
5i
Shirini F.Tajik H.Aliakbar A.Akbar A. Synth. Commun. 2001, 31: 767 -
5j
Khandekar AC.Paul AM.Khadikar BM. Synth. Commun. 2002, 32: 2931 -
6a
Mandal SK.Jensen DR.Pugsley JS.Sigman MS. J. Org. Chem. 2003, 68: 4600 -
6b
Velusamy S.Punniyamurthy T. Org. Lett. 2004, 6: 217 -
6c
Chang S.Lee M.Ko S.Lee PH. Synth. Commun. 2002, 32: 1279 - 7 For example, see:
Torii S. Electroorganic Synthesis Kodansha; Tokyo: 1985. -
8a
Chiba T.Saitoh I.Okimoto M. J. Org. Chem. 1999, 64: 2516 -
8b
Chiba T.Saitoh I.Okimoto M. Synthesis 1999, 1022 -
8c
Okimoto M.Takahashi Y. Bull. Chem. Soc. Jpn. 2002, 75: 2059 -
8d
Okimoto M.Takahashi Y. Synthesis 2002, 2215 -
8e
Okimoto M.Takahashi Y.Kakuchi T. Synthesis 2003, 2257 -
8f
Okimoto M.Nagata Y.Sueda S.Takahashi Y. Synth. Commun. 2004, 34: 281 - 9 Beilsteins Handbuch der Organischen Chemie 4th ed.: Springer; Berlin: 1943.
- 10
Ide WS.Buck JS. Org. React. 1949, 4: 269