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Volumn 6, Issue 6, 1987, Pages 1211-1218

“In-plane” Coordinated Double Bonds. Molecular Structures, Spectroscopy, and Stability of 5-methylenecyclooctene and 5-methylenecycloheptene Complexes of Platinum(II)

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EID: 0001420702     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00149a015     Document Type: Article
Times cited : (36)

References (29)
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    • Trans ligometalation: Hegedus, L. S. T etrahedron 1984 40, 2415–2434. Backvall, J. E. Acc. Chem. Res. 1983, 16, 335–342. Backvall, J. E. Acta Chem. Scand., Ser. B 1982, B36, 577–585. Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984,106, 7122–7126. Akermark, B.; Zetterberg, K. J. Am. Chem. Soc. 1984,106, 5560–5561. Sarhan, J. K. K.; Green, M.; Al-Najjar, I. M. J. Chem. Soc., Dalton Trans. 1984, 771–777. Semmelhack, M. F.; Bodurow, C. J. Am. Chem. Soc. 1984,106,1496-1498. Andell, O. S.; Backvall, J. E. J. Organomet. Chem. 1983,244, 401–407. Maresca, L.; Natile, G. J. Chem. Soc., Chem. Commun. 1983, 40–41. Hegedus, L. S.; Williams, R. E.; McGuire, M. A.; Hayashi, T. J. Am. Chem. Soc. 1980, 102, 4973–4979. cis ligand migration: (k) Doherty, N. M.; Bercaw, J. J. Am. Chem. Soc. 1985,107, 2670–2682. (1) Bryndza, H. E.; Calabrese, J. C.; Wreford, S. S. Organometallics 1984, 3,1603-1604. (m) Bryndza, H. E. Organometallics 1985, 4, 406–408. (n) Roe, D. C. J. Am. Chem. Soc. 1983,105, 7770–7771. (o) Clawson, L.; Soto, J.; Buchwald, S. L.; Steig-erwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985,107, 3377–3378. (p) Flood, T. C.; Bitler, S. P. J. Am. Chem. Soc. 1984, 106, 6076–6077. (q) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795–1803. (r) Halpern, J.; Okamoto, T. Inorg. Chim. Acta 1984, 89, L53-L54. (s) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443–1444. (t) Dekleva, T. W.; James, B. R. J. Chem. Soc., Chem. Commun. 1983, 1350–1351. (u) Drouin, M.; Harrod, J. F. Can. J. Chem. 1985, 63,353-360. (v) Fink, G.; Fenzl, W.; Mynott, R. Z. Naturforsch., B: Anorg. Chem. Org. Chem. 1985, 40B, 158–166. (w) Eisch, J. J.; Piotrowski, A. M.; Brown-stein, S. K.; Gabe, E. J.; Lee, F. L. J. Am. Chem. Soc. 1985, 107, 7219–7221.
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    • Trans ligometalation: Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1980,102,6148-6149. Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981,103, 4308–4320. Goddard, W. A., III; Steigerwald, M. L. J. Am. Chem. Soc. 1985,107, 5027–5035. Cis migration: Thorn, D. L.; Hoffman, R. J. Am. Chem. Soc. 100, 2079–2090. Backvall, J. E.; Bjorkman, E. E.; Pettersson, L.; Siegbahn, P. J. Am. Chem. Soc. 1984, 106, 4369–4373. Backvall, J. E.; Bjorkman, E. E.; Pettersson, L.; Siegbahn, P. J. Am. Chem. Soc. 1985,107, 7265–7267. Fujimoto, H.; Yamasaki, T.; Mizutani, H.; Koga, N. J. Am. Chem. Soc. 1985, 107, 6157–6161. Sakaki, S.; Kato, H.; Kanai, H.; Tarama, K. Bull. Chem. Soc. Jpn. 1975. 48. 813–818.
    • Trans ligometalation: Fujimoto, H.; Yamasaki, T. J. Am. Chem. Soc. 1986,108, 578–581. Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1980,102,6148-6149. Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981,103, 4308–4320. Goddard, W. A., III; Steigerwald, M. L. J. Am. Chem. Soc. 1985,107, 5027–5035. Cis migration: Thorn, D. L.; Hoffman, R. J. Am. Chem. Soc. 100, 2079–2090. Backvall, J. E.; Bjorkman, E. E.; Pettersson, L.; Siegbahn, P. J. Am. Chem. Soc. 1984, 106, 4369–4373. Backvall, J. E.; Bjorkman, E. E.; Pettersson, L.; Siegbahn, P. J. Am. Chem. Soc. 1985,107, 7265–7267. Fujimoto, H.; Yamasaki, T.; Mizutani, H.; Koga, N. J. Am. Chem. Soc. 1985, 107, 6157–6161. Sakaki, S.; Kato, H.; Kanai, H.; Tarama, K. Bull. Chem. Soc. Jpn. 1975. 48. 813–818.
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    • See, for examples: Principles and Applications of Organotransition University Science Books: Mill Valley, CA
    • See, for examples: Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980.
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    • Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411. Mann, B. E.; Shaw, B. L.; Shaw, G. J. Chem. Soc. A 1971, 3536–3544. Heumann, A.; Reglier, M.; Waegell, B. Angew. Chem., Int. Ed. Engl. 1979, 18, 867–868.
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    • New York, Chemical Kinetics and Reaction Mechanism; McGraw-Hill: New York, 1981. Swinehart, J. H.; Inorg. Chem. 1964, 3, 278.
    • Bernasconi, C. F. Relaxation Kinetics; Academic: New York, 1976. Espenson, J. H. Chemical Kinetics and Reaction Mechanism; McGraw-Hill: New York, 1981. Swinehart, J. H.; Castellan, G. W. Inorg. Chem. 1964, 3, 278.
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    • Kynoch: Birmingham, England Vol. IV, Table 2.2B. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A: Found. Crystallogr. 1983, A39,158. Atom coordinates for 8 taken from Syed, A.; Stevens, E. D.; Cruz, S. G. Inorg. Chem. 1984, 23, 3673–3674.
    • Cromer, D. T.; Waber, J. T. International Tables For X-ray Crystallography; Kynoch: Birmingham, England, 1974; Vol. IV, Table 2.2B. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A: Found. Crystallogr. 1983, A39,158. Atom coordinates for 8 taken from Syed, A.; Stevens, E. D.; Cruz, S. G. Inorg. Chem. 1984, 23, 3673–3674.
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    • (η3-Methallyl)(triphenylphosphine) (“in-plane” styrene)platinum(II) Similar to ref 21a except (Z)-but-2-ene “in-plane”: Miki, K.; Yamatoya, K.; Kasai, N.; Kurosawa, H.; Emoto, M.; Urabe, A. J. Chem. Soc., Chem. Commun. 1984, 1520–2.
    • (η3-Methallyl)(triphenylphosphine) (“in-plane” styrene)platinum(II) cation: Miki, K.; Kai, Y.; Kasai, N.; Kurosawa, H. J. Am. Chem. Soc. 1983, 105, 2482–2483. Similar to ref 21a except (Z)-but-2-ene “in-plane”: Miki, K.; Yamatoya, K.; Kasai, N.; Kurosawa, H.; Emoto, M.; Urabe, A. J. Chem. Soc., Chem. Commun. 1984, 1520–2.
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    • PtCl42'/alcohol/diene, “standard” conditions for (diene)PtCl2synthesis, see Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: T London
    • PtCl42'/alcohol/diene, “standard” conditions for (diene)PtCl2synthesis, see: Hartley, F. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: T London 1982 Vol. 6, pp 632-680.
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    • For effects of conformation on chelation, see
    • For effects of conformation on chelation, see: Rettig, M. F.; Wing, R. M.; Wiger, G. R. J. Am. Chem. Soc. 1981, 103, 2980–2986.
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    • Wright, L. L.; Wing, R. M.; Rettig, M. F. J. Am. Chem. Soc. 1982, 104, 610–612.
    • Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981, 103, 4308–4320. Wright, L. L.; Wing, R. M.; Rettig, M. F. J. Am. Chem. Soc. 1982, 104, 610–612.
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    • “Opposite-sign” cis and trans influences of aryl ligands have been observed in platinum-phosphorus coupling constants
    • “Opposite-sign” cis and trans influences of aryl ligands have been observed in platinum-phosphorus coupling constants: Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2117–2124.
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    • Similar NMR parameters for chloro[(1,2,5,6-η4)-cycloocta-1,5-diene] (R)platinum(II). The use of 195Pt NMR to distinguish between similar chloro and bromo complexes is well-established in coordination chemistry; see, e.g.: Harris, R. K.; Mann, B. E. NMR and the Periodic Table; Academic: New York, 1978; Pregosin, P. S. Coord. Chem. Rev. 1982, 44, 247. Pregosin, P. S. Annu. Rep. NMR Spectrosc. 1986, 17, 285 and references cited therein.
    • Similar NMR parameters for chloro[(1,2,5,6-η4)-cycloocta-1,5-diene] (R)platinum(II): Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721–727. The use of 195Pt NMR to distinguish between similar chloro and bromo complexes is well-established in coordination chemistry; see, e.g.: Harris, R. K.; Mann, B. E. NMR and the Periodic Table; Academic: New York, 1978; Pregosin, P. S. Coord. Chem. Rev. 1982, 44, 247. Pregosin, P. S. Annu. Rep. NMR Spectrosc. 1986, 17, 285 and references cited therein.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 721-727
    • Chisholm, M.H.1    Clark, H.C.2    Manzer, L.E.3    Stothers, J.B.4    Ward, J.E.H.5
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    • The ordering of the first four dienes agrees with that found for Pd(II):
    • The ordering of the first four dienes agrees with that found for Pd(II): Partenheimer, W. Inorg. Chem. 1972. 11, 743.
    • (1972) Inorg. Chem. , vol.743 , pp. 11
    • Partenheimer, W.1


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