本文研究了水溶液中γ-环糊精诱导2-萘甲酸酯的光二聚反应.γ-环糊精的限制性疏水空腔能够容纳两个2-萘甲酸甲酯(或乙酯)分子形成稳定的2:1包结复合物NA@γ-CD,光照NA@γ-CD包结物水溶液能高效、快速、高选择地生成2-萘甲酸酯的类立方烷光二聚体,并且该反应有一定程度的对映体选择性.
The photocyclodimerization of methyl (or ethyl) 2-naphthoate NA in γ-cyclodextrin aque-ous solution was investigated. Spectroscopic analyses reveal that γ-cyclodextrin can encapsulate two molecules of NA to make a stable 2:1 inclusion complex NA@γ-CD in aqueous solutions. Irradiation of NA in the γ-CD aqueous solution results in photocycloaddition with highly selectivity and efficien-cy, whereas no photocyclodimers could be detected in host-free solution.
参考文献
| [1] | Frederick D;Greene S;Misrock L;James R Wolfe J .The structure of anthracene photodimers[J].Journal of the American Chemical Society,1955,77:3852-3855. |
| [2] | Bouas L H;Castellan A;Desvergne J P .From anthracene photodimerization to jaw photochromic materials and photocrowns[J].Pure and Applied Chemistry,1980,52:2633-2648. |
| [3] | Bradshaw J S;Hammond G S .Mechanisms of photochemical reactions in solution XIX photodimerization of methyl-naphthyl ether[J].Journal of the American Chemical Society,1963,85:3953. |
| [4] | Collin P J;Roberts D B;Sugowdz G;Well D Sasse W H F .The formation of photodimers from dimethyl naphthalene-1,8-dicarboxylate methyl naphthalene-2-carboxylate[J].Tetrahedron Letters,1972,4:321-324. |
| [5] | Teitei T;Wells D;Sasse W H F .Photochemical syntheses Photodimers of derivatives of naphthalenecaboxylic acids[J].Australian Journal of Chemistry,1976,29:1783-1790. |
| [6] | Kowala C;Sugowdz G;Sasse W H F;Wunderlich J A .The X-ray analysis and molecular structure of the photodimer of methyl naphthalene-2-carboxylate[J].Tetrahedron Letters,1972,46:4721-4722. |
| [7] | Tung CH.;Wu LZ.;Zhang LP.;Chen B. .Supramolecular systems as microreactors: Control of product selectivity in organic phototransformation [Review][J].Accounts of Chemical Research,2003(1):39-47. |
| [8] | Tung CH.;Yuan ZY.;Su N.;Wu LZ. .Zeolites as templates for preparation of large-ring compounds: Intramolecular photocycloaddition of diaryl compounds[J].Journal of the American Chemical Society,1998(45):11594-11602. |
| [9] | Tung C H;Wang Y M .Lipophobic effects on photochemical and photophysical behavior of molecules with polar chains in nonpolar solvents Evidence for intermolecular aggregation and self-coiling[J].Journal of the American Chemical Society,1990,112:6322-6328. |
| [10] | Lei L;Wu LZ;Wu XL;Liao GH;Luo L;Zhang LP;Tung CH;Ding KL .Stereochemistry of a cubane-like photodimer of methyl 2-naphthoate[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2006(27):4725-4727. |
| [11] | Tamaki T;Kokubu T;Ichimura K .Regio-and stereoselective photodimerization of anthracene derivatives included by cyclodextrins[J].Tetrahedron,1987,43:1485-1494. |
| [12] | Tamagaki S;Fukuda K;Maeda H .Complexation and photodimerization of anthracene-2-sulfonate in the presence of per-6-aminocyclodextrins[J].Journal of the Chemical Society,Perkin Transactions,1995,2:389-393. |
| [13] | Moorthy J N;Venkatesan K;Weiss R G .Photodimerization of coumarins in solid cyclodextrin inclusion complexes[J].Journal of Organic Chemistry,1992,57:3292-3297. |
| [14] | Brett T J;Alexander J M;Stezowski J J .Chemical insight from crystallographic disorder-structural studies of supramelecular photochemical systems Part 21.the β-cyclodextrin-4,7-dimethylcoumarin inclusion complex:a new β-cyclodextrin dimer packing type,unanticipated photoproduct formation,and an examination of guest influence on β-CD dimer packing[J].Journal of the Chemical Society,Perkin Transactions,2000,2:1095-1104. |
| [15] | Brett T J;Alexander J M;Stezowski J J .Chemical insight from crystallographic disorder-structural studies of supra-melecular photochemical systems Part 31.the β-cyclodextrin-7-hydroxy-4-methyl coumarin inclusion complex:direct observation of photodimeriztion by X-ray crystallography[J].Journal of the Chemical Society,Perkin Transactions,2000,2:1105-1114. |
| [16] | Herrmann W;Wehrle S;Wenz G.Supramolecular control of the photochemistry of stilbenes by cyclodextrins[J].Chemical Communications,1997:1709-1711. |
| [17] | Rao K S;Hubig S M;Moorthy J N;Kochi J K .Stereoselective photodimerization of (E)-stilbenes in crystalline γ-cyclodextrin inclusion complexes[J].Journal of Organic Chemistry,1999,64:8098-8104. |
| [18] | Banu H.Shayira .Modification of photochemical reactivity of trans-2-styrylpyridine:effect of cyclodextrin complexation[J].Chemical communications,1999(7):607-608. |
| [19] | Nakamura A.;Inoue Y. .Supramolecular catalysis of the enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate by gamma-cyclodextrin[J].Journal of the American Chemical Society,2003(4):966-972. |
| [20] | Wu L Z;Chen B;Luo L;Xu H X,Liao G H.Ding K,Fan Q H.Asymmetric Catalysis:New Concept and Methods[M].北京:化学工业出版社,2008:197-249. |
| [21] | Lin Luo;Gui-Hong Liao;Xiao-Ling Wu;Lei Lei;Chen-Ho Tung;Li-Zhu Wu .γ-Cyclodextrin-Directed Enantioselective Photocyclodimerization of Methyl 3-Methoxyl-2-naphthoate[J].The Journal of Organic Chemistry,2009(9):3506-3515. |
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