イオン性界面を利用した高選択的光付加反応

概要

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Ionic olefins are adsorbed on oppositely charged surface consisted either of molecular aggregates of organic surfactants or inorganic clay interlayers. The ionic olefins, i.e., stilbazolium cations and unsaturated aromatic carboxylate anions, undergo efficient and stereoselective photocyclodimerization in the present heterogeneous reaction fields. The reaction pathways are quite different from those in solution, where no cyclodimers formed and, observed is only <I>E-Z</I> photoisomerization. Employed are not only micelle, reversed micelles, and vesicles as organic interface, but also montmorillonite and hydrotalcite clays as inorganic minerals. The stereochemistry of the resulting cyclodimers has been elucidated to be controlled by a number of factors such as orientation of the olefins in the interface of host materials, the density of ionic sites of the interface, and the looseness of the molecular packing of the guests. Mixed intercalation of different kinds of host olefins and ketone resulted in the formation of regioselective cycloadducts depending on the kinds of above mentioned ionic interface.
社団法人有機合成化学協会の論文
1996-04-01