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Volumn 18, Issue 13, 1999, Pages 2428-2439

Reactions of (chloromethyl)platinum(II) derivatives with nucleophiles. Formation of (dimethylamino)carbene complexes using N,N,N′,N′-tetramethylmethanediamine as nucleophile and the X-ray crystal and molecular structures of cis-[(Ph3P)Pt(CH2NMe3)Cl2]

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EID: 0000113346     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990049h     Document Type: Article
Times cited : (29)

References (52)
  • 18
    • 0000566619 scopus 로고
    • 2Pt(Ph)Cl] with no detectable (by NMR) dimeric product, even with a deficiency of ligand, L (Anderson, G. K.; Clark, H. C.; Davies, J. A. Inorg. Chem. 1981, 20, 3607-3611).
    • (1981) Inorg. Chem. , vol.20 , pp. 3607-3611
    • Anderson, G.K.1    Clark, H.C.2    Davies, J.A.3
  • 19
    • 85088669761 scopus 로고    scopus 로고
    • note
    • 7 in the preparation outlined in Scheme 1.
  • 20
    • 85088668856 scopus 로고    scopus 로고
    • note
    • 2OMe)Cl] may suggest that initial attack at carbon is feasible.
  • 21
    • 85088669201 scopus 로고    scopus 로고
    • note
    • 31P NMR data are collected in Tables 1 and 2, respectively.
  • 22
    • 3943075494 scopus 로고    scopus 로고
    • note
    • 3, was slowly converted into carbene complex 1a.
  • 23
    • 3943109220 scopus 로고    scopus 로고
    • note
    • Solutions of 14 show no sign of decomposition, even upon heating to 60-65°C, to give carbene complex 1a and EtOMe. Such a reaction would be analogous to the formation of 1a and trimethylamine from cyclic intermediate 2a via 3a (Scheme 1).
  • 26
    • 85088667982 scopus 로고    scopus 로고
    • note
    • 15
  • 28
    • 0141692236 scopus 로고
    • 3 did not result in an observable increase in the rate of formation of 2a, the only detectable initial products being bis(phosphine) complex 7a and free COD.
    • (1988) J. Organomet. Chem. , vol.342 , pp. 269-280
    • Thorn, D.L.1    Calabrese, J.C.2
  • 29
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    • 2Pt(R)X] (L = phosphine). See e.g.: (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2110-2116. (b) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (c) Brainard, R. L.; Miller, T. M.; Whitesides, G. M. Organometallics 1986, 5, 1481-1490. (d) Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148-156.
    • (1984) Inorg. Chem. , vol.23 , pp. 2110-2116
    • Arnold, D.P.1    Bennett, M.A.2
  • 30
    • 0000216514 scopus 로고
    • 2Pt(R)X] (L = phosphine). See e.g.: (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2110-2116. (b) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (c) Brainard, R. L.; Miller, T. M.; Whitesides, G. M. Organometallics 1986, 5, 1481-1490. (d) Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148-156.
    • (1984) Organometallics , vol.3 , pp. 1795-1803
    • Flood, T.C.1    Statler, J.A.2
  • 31
    • 0001354695 scopus 로고
    • 2Pt(R)X] (L = phosphine). See e.g.: (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2110-2116. (b) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (c) Brainard, R. L.; Miller, T. M.; Whitesides, G. M. Organometallics 1986, 5, 1481-1490. (d) Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148-156.
    • (1986) Organometallics , vol.5 , pp. 1481-1490
    • Brainard, R.L.1    Miller, T.M.2    Whitesides, G.M.3
  • 32
    • 0023101744 scopus 로고
    • 2Pt(R)X] (L = phosphine). See e.g.: (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2110-2116. (b) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (c) Brainard, R. L.; Miller, T. M.; Whitesides, G. M. Organometallics 1986, 5, 1481-1490. (d) Sen, A.; Chen, J.-T.; Vetter, W. M.; Whittle, R. R. J. Am. Chem. Soc. 1987, 109, 148-156.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 148-156
    • Sen, A.1    Chen, J.-T.2    Vetter, W.M.3    Whittle, R.R.4
  • 36
    • 3943103088 scopus 로고    scopus 로고
    • note
    • The presumed intermediate 23 has not been detected.
  • 37
    • 0001674931 scopus 로고    scopus 로고
    • For recent examples of hydrogen bonds involving four-membered rings, see: Petrucci, M. G. L.; Lebuis, A.-M.; Kakkar, A. K. Organometallics 1998, 17, 4966-4975. For a recent survey of crystal structures involving hydrogen bonds between metal-bound chlorine and hydrogen donors, including H-N groups, see: Aullon, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653-654.
    • (1998) Organometallics , vol.17 , pp. 4966-4975
    • Petrucci, M.G.L.1    Lebuis, A.-M.2    Kakkar, A.K.3
  • 38
    • 0000789060 scopus 로고    scopus 로고
    • For recent examples of hydrogen bonds involving four-membered rings, see: Petrucci, M. G. L.; Lebuis, A.-M.; Kakkar, A. K. Organometallics 1998, 17, 4966-4975. For a recent survey of crystal structures involving hydrogen bonds between metal-bound chlorine and hydrogen donors, including H-N groups, see: Aullon, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653-654.
    • (1998) Chem. Commun. , pp. 653-654
    • Aullon, G.1    Bellamy, D.2    Brammer, L.3    Bruton, E.A.4    Orpen, A.G.5
  • 40
    • 85088668095 scopus 로고    scopus 로고
    • note
    • 2)Cl]Cl (cf. phosphine analogue 17).
  • 42
    • 85088668611 scopus 로고    scopus 로고
    • note
    • 13 in the presence of excess diamine, or upon TLC of the cyclic ylide complex 2a.
  • 44
    • 0000264651 scopus 로고    scopus 로고
    • and references therein
    • Complexes of this type, containing late transition metals in high oxidation states, have been postulated as reactive intermediates in several processes. See: Alias, F. M.; Poveda, M. L.; Sellin, M.; Carmona, E. Organometallics 1998, 17, 4124-4126 and references therein.
    • (1998) Organometallics , vol.17 , pp. 4124-4126
    • Alias, F.M.1    Poveda, M.L.2    Sellin, M.3    Carmona, E.4
  • 49
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    • II species formed from certain organoplatinum-amine complexes in the presence of HX. See: (a) Wehman-Ooyevaar, I. C. M.; Grove, D. M.; de Vaal, P.; Dedieu, A.; van Koten, G. Inorg. Chem. 1992, 31, 5484-5493. (b) Wehman-Ooyevaar, I. C. M.; Grove, D. M.; Kooijman, H.; van der Sluis, P.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 9916-9924.
    • (1992) Inorg. Chem. , vol.31 , pp. 5484-5493
    • Wehman-Ooyevaar, I.C.M.1    Grove, D.M.2    De Vaal, P.3    Dedieu, A.4    Van Koten, G.5


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