Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated

VK Aggarwal, DK Dean, A Mereu…

文献索引：Aggarwal, Varinder K.; Dean, David K.; Mereu, Andrea; Williams, Richard Journal of Organic Chemistry, 2002 , vol. 67, # 2 p. 510 - 514

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被引用次数: 199

摘要

A substantial acceleration of the Baylis-Hillman reaction between cyclohexenone and benzaldehyde has been observed when the reaction is conducted in water. Several different amine catalysts were tested, and as with reactions conducted in the absence of solvent, 3- hydroxyquinuclidine was found to be the optimum catalyst in terms of rate. The reaction has been extended to other aldehyde electrophiles including pivaldehyde. Attempts to extend ...