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Synthesis 2015; 47(18): 2805-2818
DOI: 10.1055/s-0034-1380223
DOI: 10.1055/s-0034-1380223
special topic
Cycloaddition Reactions of Propyne Iminium Salts and Enol Ethers
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Further Information
Publication History
Received: 18 May 2015
Accepted after revision: 20 June 2015
Publication Date:
04 August 2015 (online)
Dedicated to Professor Manfred Regitz on the occasion of his 80th birthday
Abstract
Acetylenic iminium salts (propyne iminium salts) react with cyclic enol ethers in a thermal [2+2] cycloaddition reaction to afford condensed cyclobutene iminium salts. With acyclic enol ethers, a cycloaddition/electrocyclic ring-opening sequence occurs to give (1-alkoxybuta-1,3-dien-2-yl)methane iminium salts as mixtures of diastereoisomers. An analogous scenario is observed with 5-phenyl-2-vinylfuran as the nucleophilic olefinic component. With 1-methoxy-3-trimethylsilyloxy-1,3-butadiene, propyne iminium salts undergo a [4+2] cycloaddition. For all reactions, traces of acid must be quenched with solid K2CO3 or CaO to avoid immediate polymerization of the enol ether.
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