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Synthesis 2004(6): 831-833
DOI: 10.1055/s-2004-816000
DOI: 10.1055/s-2004-816000
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Copper(II) Tetrafluoroborate-Catalyzed Formation of Aldehyde-1,1-diacetates
Further Information
Received
21 January 2004
Publication Date:
05 March 2004 (online)
Publication History
Publication Date:
05 March 2004 (online)
Abstract
Aldehyde 1,1-diacetates are formed in excellent yields from aldehydes and acetic anhydride under solvent-free conditions at room temperature in short times in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate.
Keywords
1,1-diacetates - copper compounds - catalysis - solvent-free reactions
- 1
Gregory MJ. J. Chem. Soc. B 1970, 1201 - 2
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999. - 3
Kochhar KS.Bal BS.Deshpande RP.Rajadhyaksha SN.Pinnick HW. J. Org. Chem. 1983, 48: 1765 - 4
Sandberg M.Sydnes LK. Tetrahedron Lett. 1998, 39: 6361 ; and the references cited therein -
5a
Banks RE.Miller JA.Nunn MJ.Stanley P.Weakley TR.Ullah J. J. Chem. Soc., Perkin Trans. 1 1981, 1096 -
5b
Snider BB.Amin SG. Synth. Commun. 1978, 8: 117 -
6a
Held H.Rengstl A.Mayer D. In Ullmann’s Encyclopedia of Industrial Chemistry 5th ed., Vol. A1:Campbell FT.Pfefferkon R.Rounsaville JF. VCH; Weinheim: 1985. p.65 -
6b
Daniels W. In Kirk-Othmer Encyclopedia of Chemical Technology 3rd ed., Vol. 23:Howe-Grant M. Wiley-Interscience; New York: 1983. p.817 - 7
Frick JG.Harper RJ. J. Appl. Polym. Sci. 1984, 29: 1433 - 8
Eanderson WR. inventors; Eur. Pat. Appl. EP 125 781. ; Chem. Abstr. 1985, 102, P64010K -
9a H3PO4:
Davey W.Gwilt JR. J. Chem. Soc. 1957, 1008 -
9b H2SO4:
Tomita M.Kikuchi T.Bessho K.Hori T.Inubushi Y. Chem. Pharm. Bull. 1963, 11: 1484 -
9c HClO4:
Marshall JA.Wuts PGM. J. Org. Chem. 1977, 42: 1794 -
9d MeSO3H:
Freeman I.Karchefski EM. J. Chem. Eng. Data 1977, 22: 355 -
10a PCl3:
Michie JK.Miller JA. Synthesis 1981, 824 -
10b I2:
Deka N.Kalita DJ.Borah R.Sarma JC. J. Org. Chem. 1997, 62: 1563 -
10c NBS:
Karimi B.Seradj H.Ebrahimian GR. Synlett 2000, 623 -
11a ZnCl2:
Scriabine I. Bull. Soc. Chim. Fr. 1961, 1194 -
11b FeCl3:
Trost BM.Lee CB.Weiss JM. J. Am. Chem. Soc. 1995, 117: 7247 -
11c See also:
Wang C.Li M. Synth. Commun. 2002, 32: 3469 -
11d InCl3:
Yadav JS.Subba Rao BV.Srinivas Ch. Synth. Commun. 2002, 32: 1175 -
12a Nafion-H:
Olah GA.Mehrotra AK. Synthesis 1982, 962 -
12b Zeolites:
Kumar P.Hegde VR.Kumar TP. Tetrahedron Lett. 1995, 36: 601 -
12c See also:
Pereira C.Gigante B.Marcelo-Curto MJ.Carreyre H.Pérot G.Guisnet M. Synthesis 1995, 1077 -
12d Clays:
Zhang ZH.Li TS.Fu CG. J. Chem. Res., Synop. 1997, 174 -
12e See also:
Li TS.Zhang ZH.Gao YH. Synth. Commun. 1998, 28: 4665 -
13a LiBF4:
Sumida N.Nishioka K.Sato T. Synlett 2001, 1921 -
13b Zn(BF4)2:
Ranu BC.Dutta J.Das A. Chem. Lett. 2003, 32: 366 -
14a Sc(OTf)3:
Aggarwal VK.Fonquerna S.Venall GP. Synlett 1998, 849 -
14b Bi(OTf)3:
Carrigan MD.Eash KJ.Oswald MC.Mohan RS. Tetrahedron Lett. 2001, 42: 8133 -
14c LiOTf:
Karimi B.Maleki J. J. Org. Chem. 2003, 68: 4951 - 15
Chakraborti AK.Gulhane R. . Synthesis 2004, 111 - 16
Garrett RL. In Designing Safer Chemicals, American Chemical Society Symposium Series 640Garrett RL.De Vito SC. ACS; Washington DC: 1996. Chap. 1.