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Synthesis 2007(23): 3692-3696
DOI: 10.1055/s-2007-990881
DOI: 10.1055/s-2007-990881
PAPER
© Georg Thieme Verlag Stuttgart · New York
Chemistry of Acylals, Part IV: BF3-Catalyzed Formation of Substituted α,α′-Bis(arylmethylidene)cycloalkanones from Acylals and 1-Cycloalkenyl Trimethylsilyl Ethers
Further Information
Received
22 May 2007
Publication Date:
13 November 2007 (online)
Publication History
Publication Date:
13 November 2007 (online)
Abstract
When mixtures of an aromatic aldehyde acylal and a 1-cycloalkenyl trimethylsilyl ether in dichloromethane were treated with boron trifluoride at room temperature, the corresponding α,α′-bis(arylmethylidene)cycloalkanones were formed. The yield was sensitive to both the acetal/ether ratio and the structure of the acylal. The best results, up to 97% yield, were obtained when acylals containing a diacetoxy moiety were reacted with 1-cyclohexenyl trimethylsilyl ether with an acetal-to-ether ratio of 2:1.
Key words
acylals - bis(benzylidene)cycloalkanones - condensation - 1,1-diacyloxymethanes
- 1 The term was introduced by Hurd and Cantor, see:
Hurd CD.Cantor SM. J. Am. Chem. Soc. 1938, 60: 2677 - 2 For a review, see:
Sydnes LK.Sandberg M. Proc. Indian Natl. Sci. Acad. A: Phys. Sci. 2002, 68: 141 - 3
Yin L.Zhang Z.-H.Wang Y.-M.Pang M.-L. Synlett 2004, 1727 - 4
Artico M.Di Santo R.Costi R.Novellino E.Greco G.Massa S.Tramontano E.Marongiu ME.De Montis A.La Colla P. J. Med. Chem. 1998, 41: 3948 - 5
Costi R.Di Santo R.Artico M.Miele G.Valentini P.Novellino E.Cereseto A. J. Med. Chem. 2007, 50: 1973 - 6
Sydnes LK.Sandberg M. Tetrahedron 1997, 53: 12679 - 7
Wegschneider R.Spath E. Monatsh. Chem. 1909, 30: 825 - 8
Freeman F.Karchefsi EM. J. Chem. Eng. Data 1977, 22: 355 - 9
Pettersen EO,Larsen RO,Dornish JM,Børretsen B,Oftebro R,Ramdal T, andMoen V. inventors; PTC WO 9518607. ; Chem. Abstr. 1995, 123, 188574a - 10
Sandberg M.Sydnes LK. Org. Lett. 2000, 2: 687 - 11
Ionescu M.Makkay K. Rev. Roum. Chim. 1970, 15: 265 - 12
Scanlon WB. inventors; DE 2245518. ; Chem. Abstr. 1973, 79, 53023x - 13
Hanemann K,Schubert H,Demus D, andPelzl G. inventors; DD 115283. ; Chem. Abstr. 1977, 87, 76418j - 14
Aizenshtat Z.Hausmann M.Pickholtz Y.Tal D.Blum J. J. Org. Chem. 1977, 42: 2386 - 15
Frey H.Behrmann G.Kaupp G. Chem. Ber. 1987, 120: 387 - 16
Aoyama Y.Tanaka Y.Yoshida T.Toi H.Ogoshi H. J. Organomet. Chem. 1987, 329: 251 - 17
Lubineau A.Meyer E. Tetrahedron 1988, 44: 6065 - 18
Nakano T.Migita T. Chem. Lett. 1993, 2157 - 19
Zheng M.Wang L.Shao J.Zhong Q. Synth. Commun. 1997, 27: 351 - 20
House H.Czuba LJ.Gall M.Olmstead HD. J. Org. Chem. 1969, 34: 2324