Methyl-2,5-diphenyl-4-styrylimidazole

The 4-styryl products are of value in that they offer an alternative route to imidazole-4-carbaldchydes when they are oxidized by osmium tetroxide and sodium periodate in about 70% yield [20]. 

The most recent synthetically useful modification of TOSMIC reactions involves the cycloaddition of Af-trimethylsilylimines with lithiotosylmethyl isocyanides. This allows the preparation of 4-mono- and 4,5-disubstituted imidazoles from readily accessible aldehydes and organolithium compounds in a one-pot reaction. Although yields are only moderate, there are advantages which accrue from the easy availability of the starting 

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Vinyl and ethynyl groups attached to an imidazole ring can be catalytically reduced to the saturated (or less unsaturated) species and cleaved by oxidation. The corresponding 4-carbaldehyde is formed in 71% yield when l-methyl-2,5-diphenyl-4-styrylimidazole is oxidized with osmium tetroxide. However, they may not react like aliphatic alkenes and alkynes not all addition reactions occur normally, Michael additions are known, and the compounds can act as dienophiles in DielsAlder reactions (e.g., Scheme 132). 

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