Reactions of haloarenes, haloheteroarenes and dihalobenzenes with triphenylstannyl anions in DMSO and acetonitrile

Journal of Organometallic Chemistry

Volumn 582, Issue 2, 1999, Pages 229-234

  Lockhart, María T ^a   Chopa, Alicia B ^a   Rossi, Roberto A ^b  

^a UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

^b UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

HME; Ph3Sn ions; Photostimulation; SRN1 Reactions

Indexed keywords

EID: 0000768252     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00040-6     Document Type: Article

References (29)

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9. RN1 Mechanism; ACS Monograph 178; Washington, DC 1983. (b) W.R. Bowman, Chem. Soc. Rev. 17 (1988) 283. (c) R.K. Norris, in: B.M. Trost (Ed.), Comprehensive Organic Synthesis, vol. 4, Pergamon, New York, 1991, p. 451. (d) R.A. Rossi, A.B Pierini, A.B. Peñéñory, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Functional Group, Wiley, Chichester, Supl. D2, Ch 24, 1995, p.1395.
10. RN1 Mechanism; ACS Monograph 178; Washington, DC 1983. (b) W.R. Bowman, Chem. Soc. Rev. 17 (1988) 283. (c) R.K. Norris, in: B.M. Trost (Ed.), Comprehensive Organic Synthesis, vol. 4, Pergamon, New York, 1991, p. 451. (d) R.A. Rossi, A.B Pierini, A.B. Peñéñory, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Functional Group, Wiley, Chichester, Supl. D2, Ch 24, 1995, p.1395.
11. RN1 Mechanism; ACS Monograph 178; Washington, DC 1983. (b) W.R. Bowman, Chem. Soc. Rev. 17 (1988) 283. (c) R.K. Norris, in: B.M. Trost (Ed.), Comprehensive Organic Synthesis, vol. 4, Pergamon, New York, 1991, p. 451. (d) R.A. Rossi, A.B Pierini, A.B. Peñéñory, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Functional Group, Wiley, Chichester, Supl. D2, Ch 24, 1995, p.1395.
12. 3CN are suitable solvents by this type of mechanism, despite they are better hydrogen donors than liquid ammonia. See (a) J.F. Bunnett, R.G. Scamehorn, R.P. Traber, J. Org. Chem. 41 (1976) 3677. (b) M.P. Moon, J.F.Wolfe, J. Org. Chem. 44 (1979) 4081.
13. 3CN are suitable solvents by this type of mechanism, despite they are better hydrogen donors than liquid ammonia. See (a) J.F. Bunnett, R.G. Scamehorn, R.P. Traber, J. Org. Chem. 41 (1976) 3677. (b) M.P. Moon, J.F.Wolfe, J. Org. Chem. 44 (1979) 4081.
14. J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508. For a review see: V. Farina, V. Krishnamurthy, W.J. Scott, in: L.A. Paquette, Ed.), The Stille Reaction, Organic Reactions, vol. 50, 1997.
15. J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508. For a review see: V. Farina, V. Krishnamurthy, W.J. Scott, in: L.A. Paquette, Ed.), The Stille Reaction, Organic Reactions, vol. 50, 1997.
16. 3SnH is ca. 16 (E.S. Petrov, M.I. Terekhova, R.G. Mirskov, M.G. Voronkov, A.I. Shatenshtein, Dokl. Akad. Nauk. SSSR, 221 (1975) 111; Chem. Abstr. 82 (1975) 155040e), lower than that of t-BuOH in DMSO (32.2) (F.G. Bordwell, Acc. Chem. Res. 21 (1988) 456).
17. 3SnH is ca. 16 (E.S. Petrov, M.I. Terekhova, R.G. Mirskov, M.G. Voronkov, A.I. Shatenshtein, Dokl. Akad. Nauk. SSSR, 221 (1975) 111; Chem. Abstr. 82 (1975) 155040e), lower than that of t-BuOH in DMSO (32.2) (F.G. Bordwell, Acc. Chem. Res. 21 (1988) 456).
18. 3SnH is ca. 16 (E.S. Petrov, M.I. Terekhova, R.G. Mirskov, M.G. Voronkov, A.I. Shatenshtein, Dokl. Akad. Nauk. SSSR, 221 (1975) 111; Chem. Abstr. 82 (1975) 155040e), lower than that of t-BuOH in DMSO (32.2) (F.G. Bordwell, Acc. Chem. Res. 21 (1988) 456).
19. 3Sn)O, indicating that this is an HME reaction.
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23. - ions, see Ref. [4].
24. - ions, see Ref. [4].
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