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Volumn 68, Issue 20, 2003, Pages 7833-7840

Highly efficient photochemical generation of a triple bond: Synthesis, properties, and photodecarbonylation of cyclopropenones

Author keywords

[No Author keywords available]

Indexed keywords

LASER FLASH PHOTOLYSIS;

EID: 0141765936     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034869m     Document Type: Article
Times cited : (96)

References (62)
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    • Potts, K. T.; Baum, J. S. Chem. Rev. 1974, 74, 189. Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; pp 1300-1311.
    • (1974) Chem. Rev. , vol.74 , pp. 189
    • Potts, K.T.1    Baum, J.S.2
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    • 0000511262 scopus 로고
    • Rappoport, Z., Ed.; Wiley: New York
    • Potts, K. T.; Baum, J. S. Chem. Rev. 1974, 74, 189. Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; pp 1300-1311.
    • (1987) The Chemistry of the Cyclopropyl Group , pp. 1300-1311
    • Halton, B.1    Banwell, M.G.2
  • 11
    • 0000223882 scopus 로고
    • Ciabattoni, J.; Nathan, E. C. J. Am. Chem. Soc. 1969, 91, 4766. Dehmlow, E. V.; Neuhaus, R.; Schell, H. G. Chem. Ber. 1988, 121, 569. Dehmlow, S. S.; Dehmlow, E. V. Z. Naturforsch. B 1975, 30b, 404. Dehmlow, E. V. Leib. Ann. 1969, 729, 64.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 4766
    • Ciabattoni, J.1    Nathan, E.C.2
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    • 0037600006 scopus 로고
    • Ciabattoni, J.; Nathan, E. C. J. Am. Chem. Soc. 1969, 91, 4766. Dehmlow, E. V.; Neuhaus, R.; Schell, H. G. Chem. Ber. 1988, 121, 569. Dehmlow, S. S.; Dehmlow, E. V. Z. Naturforsch. B 1975, 30b, 404. Dehmlow, E. V. Leib. Ann. 1969, 729, 64.
    • (1988) Chem. Ber. , vol.121 , pp. 569
    • Dehmlow, E.V.1    Neuhaus, R.2    Schell, H.G.3
  • 13
    • 0000223882 scopus 로고
    • Ciabattoni, J.; Nathan, E. C. J. Am. Chem. Soc. 1969, 91, 4766. Dehmlow, E. V.; Neuhaus, R.; Schell, H. G. Chem. Ber. 1988, 121, 569. Dehmlow, S. S.; Dehmlow, E. V. Z. Naturforsch. B 1975, 30b, 404. Dehmlow, E. V. Leib. Ann. 1969, 729, 64.
    • (1975) Z. Naturforsch. B , vol.30 B , pp. 404
    • Dehmlow, S.S.1    Dehmlow, E.V.2
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    • 84982062784 scopus 로고
    • Ciabattoni, J.; Nathan, E. C. J. Am. Chem. Soc. 1969, 91, 4766. Dehmlow, E. V.; Neuhaus, R.; Schell, H. G. Chem. Ber. 1988, 121, 569. Dehmlow, S. S.; Dehmlow, E. V. Z. Naturforsch. B 1975, 30b, 404. Dehmlow, E. V. Leib. Ann. 1969, 729, 64.
    • (1969) Leib. Ann. , vol.729 , pp. 64
    • Dehmlow, E.V.1
  • 26
    • 0003509303 scopus 로고
    • This procedure has been used for the preparation of a series of arylhydroxycyclopropenones: (a) Chicos, J. C.; Patton, E.; West, R. J. Org. Chem. 1974, 39, 1647.
    • (1974) J. Org. Chem. , vol.39 , pp. 1647
    • Chicos, J.C.1    Patton, E.2    West, R.3
  • 27
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    • Also see ref 1. Direct quenching of arylcyclopropenium cation with water, on the other hand, results in ring openinig and formation of 2-aryl-3-chloroacrylic acid: (b) West, R.; Zecher, D. C.; Tobey, S. W. J. Am. Chem. Soc. 1970, 92, 168.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 168
    • West, R.1    Zecher, D.C.2    Tobey, S.W.3
  • 44
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    • note
    • The geometry of phenyl- and diphenylcyclopropenones was optimized at the DFT B3LYP/6-311+G(3df, 2p) level by using the Gaussian 98W program as discussed in the Experimental Section.
  • 49


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