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-00000084.xml
Synthesis 2003(12): 1881-1882
DOI: 10.1055/s-2003-40983
DOI: 10.1055/s-2003-40983
SHORTPAPER
© Georg ThiemeVerlag Stuttgart · New York
Antimony Pentachloride-PromotedRegeneration of Carbonyl Compounds from Oximes [1]
Further Information
Received
16 April 2003
Publication Date:
30 July 2003 (online)
Publication History
Publication Date:
30 July 2003 (online)
Abstract
A simple and convenient method for the cleavage of oximes totheir parent aldehydes and ketones using antimony pentachlorideis described.
Key words
oximes - antimony pentachloride - cleavagereaction
-
1a
Chermis ND.Entrikin JB. Identification of Organic Compounds WileyInterscience; New York: 1963. -
1b
Barton DHR.Beaton JM.Geller LE.Pechet MM. J. Am. Chem. Soc 1961, 83: 4076 -
1c
Barton DHR.Beaton JM. J.Am. Chem. Soc. 1961, 83: 4083 - 2
Kabalka GW.Pace RD.Wadgaonkar PP. Synth. Commun. 1990, 20: 2453 - 3
Greene JG.Wuts PGM. Protecting Groups in Organic Synthesis Wiley; NewYork: 1991. p.175-223 - 4
Whitesell JK.Whitesell MA. Synthesis 1983, 517 ; and references cited therein - 5
Donaruma LG.Helolt WZ. Org. React. 1960, 11: 1 -
6a
Donaldson RE.Saddler JC.Byrn S.McKenzie AT.Fuchs PL. J.Org. Chem. 1983, 48: 2167 -
6b
Corsaro A.Ugo Ch.Pistara V. Synthesis 2001, 1903 -
6c
Habib F.Jamalian A.Karimi B. Bull.Chem. Soc. Jpn. 2002, 75: 1761 -
6d
Hangarge RV.Mane AS.Chavan VP.Shingare MS. Indian.J. Chem., Sect. B 2002, 41: 1302 -
7a
Curran DP.Brill JF.Rakiewicz DM. J.Org. Chem. 1984, 49: 1654 -
7b
Drabowicz J. Synthesis 1980, 125 -
7c
Corey EJ.Hopkins PB.Kim S.Yoo S.Nambiar KP.Flack JR. J.Am. Chem. Soc. 1979, 101: 7131 -
8a
Chrisman W.Blankinship MJ.Taylor B.Haris CE. TetrahedronLett. 2001, 42: 4775 -
8b
Rao CG.Krishna AHR.Singh BB.Bhatnagar SP. Synthesis 1983, 808 -
8c
Verma RS.Mesharam HM. Tetrahedron Lett. 1997, 38: 5427 -
8d
Nattier BA.Eash KJ.Mohan RS. Syntheisis 2001, 1010 -
8e
Olah GA.Liao Q.Lee CS.Prakash GKS. Synlett 1993, 427 -
8f
Bose DS.Narsaiah AV. Synth.Commun. 1999, 29: 937 -
8g
Bose DS.Narsaiah AV. Synth.Commun. 2000, 30: 3121 -
8h
Bose DS.Narsaiah AV. Synth.Commun. 2000, 30: 1153 -
8i
Khazaci A.Vaghei RG. Tetrahedron Lett. 2002, 43: 3073 -
8j
Shaker SC.Gopalaiah K. TetrahedronLett. 2002, 43: 4023 -
8k
Sandhu JS.Boruah A.Boruah B.Prajapati D. TetrahedronLett. 1997, 38: 4267 -
8l
Hashemi MM.Beni YA. Synth.Commun. 2001, 31: 295 -
8m
Geneste F.Racelma M.Moradpour A. Synth. Commun. 1997, 27: 957 -
8n
Lee JG.Hwang JP. Chem. Lett. 1995, 507 -
8o
Baruah JB.Sen K. Indian J. Chem., Sect.A 1993, 32: 980 -
8p
Hajipour AR.Mallakpour SE.Baltork IM.Backnejad H. IndianJ. Chem., Sect. B 2002, 41: 1302 -
8q
Demir AS.Tanyeli C.Altinel E. Tetrahedron. Lett. 1997, 38: 7267 -
9a
Laszlo P.Polla S. Synthesis 1985, 439 -
9b
Heravi MM.Tajbakhsh M. Phosphorus,Sulfur, Silicon Relat. Elem. 2001, 176: 195 -
10a
Hajipour AR.Mallapour SE.Shoee S. Synth. Commun. 2002, 32: 9 -
10b
Varma RS.Meshram HM. Tetrahedron.Lett. 1997, 38: 7973 -
10c
Heravi MM.Ajami D.Mohajerani B.Hyder KT.Mitra G. Synth. Commun. 2002, 32: 3325 - 11
Sheldon RA. CHEMTECH 1991, 566 - 12
Olah GA.Kobayashi S.Tashiro M. J.Am. Chem. Soc. 1972, 94: 7448