The selective functionalization of saturated hydrocarbons. Part 40. Aspects of Fe(II) based peroxide fragmentation in pyridine solution

Tetrahedron

Volumn 53, Issue 43, 1997, Pages 14565-14578

  Barton, Derek H R ^a   Launay, Franck ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FERROUS ION; HYDROPEROXIDE; PYRIDINE; TETRAHYDROFURAN;

ARTICLE; DECOMPOSITION; ELECTRON TRANSPORT; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

HABER;

EID: 0030801585     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01063-6     Document Type: Article

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49. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
50. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
51. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
52. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
53. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
54. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
55. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
56. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
57. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
58. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
59. Posner, G.H.; Gonzalez, L.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Tetrahedron 1997, 53, 37-50. Posner, G.H.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. Tetrahedron Lett. 1996, 37, 7225-7228 . Posner, G.H.; Wang, D.; Gonzalez, L.; Tao, X.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A. ibid. 1996, 37, 815-818 and included references Posner, G.H.; Park, S.B.; Gonzalez, L.; Wang, D.; Cumming, J.N.; Klinedinst, D.; Shapiro, T.A.; Bachi, M.D. J. Am. Chem. Soc. 1996, 118, 3537-3538. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chem. Acta 1996, 79, 1475-1487. Bloodworth, A.J.; Shah, A. Tetrahedron Lett. 1995, 36, 7551-7554. Porter, N.A.; Mebane, R.C. Tetrahedron Lett. 1982, 23, 2289-2292. Wu, W.-M.; Yao, Z.-J.; Wu, Y.L.; Jiang, K.; Wang, Y.F.; Chen, H.B.; Shan, F.; Li, Y. Chem. Commun. 1996, 2213-2214. Haynes, R.K.; Vonwiller, S.C Tetrahedron Lett. 1996, 37, 253-256. Haynes, R.K.; Vonwiller, S.C. ibid. 1996, 37, 257-260. Brown, D.; Davis, B.T.; Halsall, T.G.; Hands, A.R. J. Chem. Soc. 1962, 4492-4496. The nucleophilic attack of the O-O bond by Fe(II) has already been mentioned as a plausible hypothesis to explain the ferrous-induced decomposition of epidioxides, see: Herz, W.; Ligon, R.C.; Turner, J.A.; Blount, J.F. J. Org. Chem. 1977, 42, 1885-1895.
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