Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
2,4-Dienals were synthesized conveniently by using a new formylenylolefination method. The aldehydes were reacted with formylallyltriphenylarsonium bromide (2) in Et2O—THF—H2O (9 : 1 : 0.05) in the presence of K2CO3 at room temperature to give (2E,4E)-and (2E,4Z)-dienals, in favor of the former. They could be easily separated by chromatography, and the latter, in CH2Cl2, could be converted to the former on treatment with a catalytic amount of iodine in daylight. The configurations of the (E,E) products have been conveniently identified by 1H NMR determined in C6D6. The syntheses of two natural products, navenone A and Otanthus maritima amide, by this method are also reported in detail.
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