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Volumn 125, Issue 11, 2003, Pages 3243-3247

Cavity-directed synthesis within a self-assembled coordination cage: Highly selective [2 + 2] cross-photodimerization of olefins

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION REACTIONS; DIMERIZATION; DIMERS; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

EID: 0037454330     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020718+     Document Type: Article
Times cited : (283)

References (43)
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    • Diels-Alder reactions in self-assembled cage compounds take place via ternary complexes. (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. (c) Kang, J.: Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389.
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    • Diels-Alder reactions in self-assembled cage compounds take place via ternary complexes. (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. (c) Kang, J.: Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389.
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    • [2 + 2] cross-photodimerization in the crystal state: (a) Ramamurthy, V. Tetrahedron 1986, 42, 5753.
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    • In general, photodimerization of two different olefins gives a homo/cross mixture: (a) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Commun. 1998, 2093. (b) Haga, N.; Nakajima, H.; Takayanagi, H.; Tokumaru, K. J. Org. Chem. 1998, 63, 5372. (c) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Lett. 2001, 448. (d) Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 2002, 734.
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    • In general, photodimerization of two different olefins gives a homo/cross mixture: (a) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Commun. 1998, 2093. (b) Haga, N.; Nakajima, H.; Takayanagi, H.; Tokumaru, K. J. Org. Chem. 1998, 63, 5372. (c) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Lett. 2001, 448. (d) Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 2002, 734
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  • 33
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    • In general, photodimerization of two different olefins gives a homo/cross mixture: (a) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Commun. 1998, 2093. (b) Haga, N.; Nakajima, H.; Takayanagi, H.; Tokumaru, K. J. Org. Chem. 1998, 63, 5372. (c) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Lett. 2001, 448. (d) Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 2002, 734
    • (2001) Chem. Lett. , pp. 448
    • Haga, N.1    Takayanagi, H.2    Tokumaru, K.3
  • 34
    • 0036009269 scopus 로고    scopus 로고
    • In general, photodimerization of two different olefins gives a homo/cross mixture: (a) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Commun. 1998, 2093. (b) Haga, N.; Nakajima, H.; Takayanagi, H.; Tokumaru, K. J. Org. Chem. 1998, 63, 5372. (c) Haga, N.; Takayanagi, H.; Tokumaru, K. Chem. Lett. 2001, 448. (d) Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 2002, 734
    • (2002) J. Chem. Soc., Perkin Trans. 2 , pp. 734
    • Haga, N.1    Takayanagi, H.2    Tokumaru, K.3
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    • note
    • (f) Coordination cage 1 is now commercially available from Wako Chemical Co. Ltd. (Pd-Nanocage).
  • 41
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    • note
    • The photoirradiation of an aqueous solution of 1 and 3a (1:2 ratio) gave no adducts under the same conditions (400 W, 3 h).
  • 42
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    • note
    • The equilibration of eq 4 should be rapid on the NMR time scale because averaged signals for guest 2 were observed when excess 2 was added. Thus, the selective formation of the cross-dimer may be interpreted by the rapid consumption of the hetero pair from an equilibrium mixture of eq 4. However, because of the remarkable steric effect on the substrate, we consider the selective formation of the hetero pair rather than the rapid consumption. equation presented


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