Chemistry of Acylals, Part IV: BF3-Catalyzed Formation of Substituted α,α′-Bis(arylmethylidene)cycloalkanones from Acylals and 1-Cycloalkenyl Trimethylsilyl Ethers

Leiv K. Sydnes; Gry S. Pedersen; Bjarte Holmelid; Marcel Sandberg

doi:10.1055/s-2007-990881

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Synthesis 2007(23): 3692-3696
DOI: 10.1055/s-2007-990881

PAPER

Chemistry of Acylals, Part IV: BF₃-Catalyzed Formation of Substituted α,α′-Bis(arylmethylidene)cycloalkanones from Acylals and 1-Cycloalkenyl Trimethylsilyl Ethers

Leiv K. Sydnes*^a, Gry S. Pedersen^a, Bjarte Holmelid^a, Marcel Sandberg^a,b
^a Department of Chemistry, University of Bergen, Allégt. 41, 5007 Bergen, Norway
Fax: +4755589490; e-Mail: leiv.sydnes@kj.uib.no;
^b Synthetica AS, Forskningsparken, Gaustadalléen 21, 0349 Oslo, Norway

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Publication History

Received 22 May 2007
Publication Date:
13 November 2007 (online)

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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

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