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Volumn 15, Issue 24, 1996, Pages 5080-5084

Photolytic reaction of hydroxy fischer carbene complexes: Synthesis of α-hydroxy esters

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EID: 0006573975     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960530x     Document Type: Article
Times cited : (8)

References (66)
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    • Merino, I.1    Hegedus, L.S.2
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    • For recent papers, see: (a) Reed, A. D.; Hegedus, L. S. J. Org. Chem. 1995, 60, 3787. (b) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522. (c) Robbing, S.; Mattay, J.; Raabe, G. Chem. Ber. 1993, 126, 1849.
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    • For recent papers, see: (a) Zhu, J.; Hegedus. L. S. J. Org. Chem. 1995, 60, 5831. (b) Dubuisson, C.; Fukumoto, Y.; Hegedus, L. S. J. Am. Chem. Soc. 1995, 117, 3697.
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    • For some other related α-hydroxy complexes of Cr, W, and Re, see: (a) Dötz, K. H. Chem. Ber. 1985, 118, 1126. (b) Weiss, K.; Fischer, E. O. Chem. Ber. 1976, 109, 1120. (c) Fischer, E. O.; Riedel, W. E. Chem. Ber. 1968, 88, 156.
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    • For some other related α-hydroxy complexes of Cr, W, and Re, see: (a) Dötz, K. H. Chem. Ber. 1985, 118, 1126. (b) Weiss, K.; Fischer, E. O. Chem. Ber. 1976, 109, 1120. (c) Fischer, E. O.; Riedel, W. E. Chem. Ber. 1968, 88, 156.
    • (1976) Chem. Ber. , vol.109 , pp. 1120
    • Weiss, K.1    Fischer, E.O.2
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    • For some other related α-hydroxy complexes of Cr, W, and Re, see: (a) Dötz, K. H. Chem. Ber. 1985, 118, 1126. (b) Weiss, K.; Fischer, E. O. Chem. Ber. 1976, 109, 1120. (c) Fischer, E. O.; Riedel, W. E. Chem. Ber. 1968, 88, 156.
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    • note
    • The use of Chemical Abstracts Service names has been attempted throughout this paper.
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    • A different decomposition route has been observed using bimetallic carbene complexes. Erker, G.; Sosna, F. Organometallics 1990, 9, 1949.
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    • Erker, G.1    Sosna, F.2
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    • For some recent syntheses of α-hydroxy acid esters, see: (a) Julia, M.; Pfeuty-Saint James, V.; Ple, K.; Verpeaux, J.-N.; Hollingworth, G. Bull. Soc. Chim. Fr. 1996, 133, 15. (b) Satoh, T.; Onda, K.-I.; Yamakawa, K. J. Org. Chem. 1991, 56, 4129. (c) Orito, K.; Seki, Y.; Suginome, H.; Iwadare, T. Bull. Chem. Soc. Jpn. 1989, 62, 2013.
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    • For some recent syntheses of α-hydroxy acid esters, see: (a) Julia, M.; Pfeuty-Saint James, V.; Ple, K.; Verpeaux, J.-N.; Hollingworth, G. Bull. Soc. Chim. Fr. 1996, 133, 15. (b) Satoh, T.; Onda, K.-I.; Yamakawa, K. J. Org. Chem. 1991, 56, 4129. (c) Orito, K.; Seki, Y.; Suginome, H.; Iwadare, T. Bull. Chem. Soc. Jpn. 1989, 62, 2013.
    • (1991) J. Org. Chem. , vol.56 , pp. 4129
    • Satoh, T.1    Onda, K.-I.2    Yamakawa, K.3
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    • 0003031180 scopus 로고    scopus 로고
    • For some recent syntheses of α-hydroxy acid esters, see: (a) Julia, M.; Pfeuty-Saint James, V.; Ple, K.; Verpeaux, J.-N.; Hollingworth, G. Bull. Soc. Chim. Fr. 1996, 133, 15. (b) Satoh, T.; Onda, K.-I.; Yamakawa, K. J. Org. Chem. 1991, 56, 4129. (c) Orito, K.; Seki, Y.; Suginome, H.; Iwadare, T. Bull. Chem. Soc. Jpn. 1989, 62, 2013.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 2013
    • Orito, K.1    Seki, Y.2    Suginome, H.3    Iwadare, T.4
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    • 85033861129 scopus 로고    scopus 로고
    • note
    • Due to their instability on silica gel, upon isolation of the acetals a small amount impurity was always obtained. Correct elemental analyses could not be obtained from 16 and 22.
  • 43
    • 85033868368 scopus 로고    scopus 로고
    • note
    • The deep red color of the hydroxy carbene solution immediately changed to yellow, the color of the tetramethylammonium salt, upon addition of the amine.
  • 48
    • 85033838133 scopus 로고    scopus 로고
    • note
    • 1H FT-NMR Spectra # 2,1220 A, and The Aldrich Library of FT-IR Spectra #2, 281 C.
  • 49
    • 85033841517 scopus 로고    scopus 로고
    • note
    • 1H FT-NMR Spectra # 2,1221 A, and The Aldrich Library of FT-IR Spectra # 2, 271 C.
  • 51
    • 85033836231 scopus 로고    scopus 로고
    • note
    • 1H FT-NMR Spectra # 1,1033 C, and The Aldrich Library of FT-IR Spectra # 1, 659 B.
  • 52
    • 85033833327 scopus 로고    scopus 로고
    • note
    • The formation of a pink suspension in place of a faint yellow solution was observed in all cases where an acetal was formed. Upon addition of water, the suspension dissolves and changes color producing a light green aqueous phase.
  • 59
    • 85033869784 scopus 로고    scopus 로고
    • note
    • From chromium hexacarbonyl and sec-butyllithium followed by treatment of the intermediate lithium salt with tetramethylammonium chloride as described by Fischer and Maasböl in ref 17g.


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