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Volumn 102, Issue 35, 1998, Pages 6993-7000

Comparative ab initio treatment (hartree-fock, density functional theory, MP2, and quadratic configuration interactions) of the cycloaddition of phosphorus ylides with formaldehyde in the gas phase

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EID: 0010431797     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp981085h     Document Type: Article
Times cited : (25)

References (75)
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    • Kojima, S.1    Kawaguchi, K.2    Akiba, K.3
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    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1549
    • Bojin, M.L.1    Barkallah, S.2    Evans, S.A.3
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    • For recent contributions see the following. (a) Nishizawa, M.; Komatsu, Y.; Garcia, D. M.; Noguchi, Y.; Imagawa, H.; Yamada, H. Tetrahedrom Lett. 1997, 38, 1215. (b) Reynolds, K. A.; Finn, M. G. J. Org. Chem. 1997, 62, 2574. (c) Kojima, S.; Kawaguchi, K.; Akiba, K. Tetrahedrom Lett. 1997, 38, 7753. (d) Kojima, S.; Takagi, R.; Akiba, K. J. Am. Chem. Soc. 1997, 119, 5970. (e) Klar, U.; Deicke, P. Tetrahedrom Lett. 1996, 37, 4141. (f) Yamataka, H.; Takatsuka, T.; Hanafusa, T. J. Org, Chem. 1996, 61, 722. (g) Bojin, M. L.; Barkallah, S.; Evans, S. A. J. Am. Chem. Soc. 1996, 118, 1549. (h) Takeuchi, K.; Paschal, J. W.; Loncharich, R. J. J. Org. Chem. 1995, 60, 156.
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    • note
    • 8 has been recently reported. In the semistabilized case, a dibenzophosphole-substituted phosphorus atom in the oxaphosphetane is stabilized relative to the phosphine oxide product; hence, the decomposition rate is retarded. In the stabilized case, resistance to oxaphosphetane decomposition is provided by the stabilizing effects of electron-withdrawing groups and ring strain on the phosphorus atom.
  • 24
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  • 58
    • 11744342409 scopus 로고    scopus 로고
    • note
    • Certain commercial materials and equipment are identified in this paper in order to specify procedures completely. In no case does such identification imply recommendation or endorsement by the National Institute of Standards and Technology nor does it imply that the material or equipment identified is necessarily the best available for the purpose.
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    • Issues regarding the electronic nature of phosphonium ylides have been extensively revised, see the following. Gilheany, D. G. Chem. Rev. 1994, 94, 1339.
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    • Gilheany, D.G.1


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