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Volumn 122, Issue 36, 2000, Pages 8795-8796

Supramolecular catalysis of olefin [2 + 2] photodimerization [10]

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINNAMIC ACID;

EID: 0034644385     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002089e     Document Type: Letter
Times cited : (96)

References (24)
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  • 5
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    • Solid-state control of photoreactivity is much more common, for recent overviews see: Ito, Y. Synthesis 1998, 1. Feldman, K. S.; Campbell, R. F.; Saunders, J. C.; Ahn, C.; Masters, K. M. J. Org. Chem. 1997, 62, 8814.
    • (1998) Synthesis , pp. 1
    • Ito, Y.1
  • 7
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    • Hydrogen-bonding has been used to direct photocycloaddtion reactions in solution: (a) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650. (b) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1997, 119, 10237. (c) Sieburth, S. McN.; McGee, K. F., Jr.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10650
    • Bach, T.1    Bergmann, H.2    Harms, K.3
  • 8
    • 0030682460 scopus 로고    scopus 로고
    • Hydrogen-bonding has been used to direct photocycloaddtion reactions in solution: (a) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650. (b) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1997, 119, 10237. (c) Sieburth, S. McN.; McGee, K. F., Jr.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10237
    • Crimmins, M.T.1    Choy, A.L.2
  • 9
    • 0032573872 scopus 로고    scopus 로고
    • Hydrogen-bonding has been used to direct photocycloaddtion reactions in solution: (a) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650. (b) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1997, 119, 10237. (c) Sieburth, S. McN.; McGee, K. F., Jr.; Al-Tel, T. H. J. Am. Chem. Soc. 1998, 120, 587.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 587
    • McN, S.S.1    McGee K.F., Jr.2    Al-Tel, T.H.3
  • 14
    • 0343240867 scopus 로고    scopus 로고
    • note
    • Compound 1 was prepared by Heck coupling between 2-amino-4-(4-iodophenyl)amino-6-methoxy[1, 3, 5]triazine and methylacrylate in 68% yield. Experimental details will be published elsewhere.
  • 19
    • 0001490606 scopus 로고    scopus 로고
    • Zerkowski, J. A.; MacDonald, J. C.; Seto, C. T.; Wierda, D. A.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 2382. For a recent overview, see Ariga, K.; Kunitake, Y. Acc. Chem. Res. 1998, 31, 371.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 371
    • Ariga, K.1    Kunitake, Y.2
  • 22
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    • The formation of head-to-tail dimers is more commonly observed in the solid. Crystal engineering can favor the formation of the ε-truxillate dimer [Ito, Y.; Borecka, B.; Scheffer, J, R.; Trotter, J. Tetrahedron Lett. 1995, 36, 6083], as can the use of Lewis acids in solution [ref 6].
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6083
    • Ito, Y.1    Borecka, B.2    Scheffer, J.R.3    Trotter, J.4
  • 23
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    • note
    • 2, 400 MHz).
  • 24
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    • The observed binding constant is comparable to that reported in ref 9, but lower than those for tailored barbiturate receptors [Chang, S. K.; Van Engen, D.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640].
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7640
    • Chang, S.K.1    Van Engen, D.2    Fan, E.3    Hamilton, A.D.4


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