Thermal Decomposition of Pentacarbonyl(1-acyloxyalkylidene)chromium(0) Complexes: Formation of Z-Enol Esters

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5945-5952

  Söderberg, Björn C ^a   Liu, Jian ^a   Ball, Thomas W ^b   Turbeville, Michael J ^b  

^a WEST VIRGINIA UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042004866     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962197c     Document Type: Article

References (75)

1. To our knowledge, pentacarbonyl[1-acyloxy(2-furyl)methylidene]- chromium(0) and pentacarbonyl[1-acyloxy(2-thienyl)methylidene]chromium(0) are the only acyloxy chromium complexes isolable at room temperature. (a) Connor, J. A.; Jones, E. M. J. Chem. Soc. A 1971, 1974. (b) Fischer, E. O.; Selmayr, T.; Kreissl, F. R. Chem. Ber. 1977, 110, 2947. For an attempted intramolecular benzannulation of a related furyl complex, see: Wulff, W. D.; McCallum, J. S.; Kunng, F.- A. J. Am. Chem. Soc. 1988, 110, 7419.
2. To our knowledge, pentacarbonyl[1-acyloxy(2-furyl)methylidene]- chromium(0) and pentacarbonyl[1-acyloxy(2-thienyl)methylidene]chromium(0) are the only acyloxy chromium complexes isolable at room temperature. (a) Connor, J. A.; Jones, E. M. J. Chem. Soc. A 1971, 1974. (b) Fischer, E. O.; Selmayr, T.; Kreissl, F. R. Chem. Ber. 1977, 110, 2947. For an attempted intramolecular benzannulation of a related furyl complex, see: Wulff, W. D.; McCallum, J. S.; Kunng, F.- A. J. Am. Chem. Soc. 1988, 110, 7419.
3. To our knowledge, pentacarbonyl[1-acyloxy(2-furyl)methylidene]- chromium(0) and pentacarbonyl[1-acyloxy(2-thienyl)methylidene]chromium(0) are the only acyloxy chromium complexes isolable at room temperature. (a) Connor, J. A.; Jones, E. M. J. Chem. Soc. A 1971, 1974. (b) Fischer, E. O.; Selmayr, T.; Kreissl, F. R. Chem. Ber. 1977, 110, 2947. For an attempted intramolecular benzannulation of a related furyl complex, see: Wulff, W. D.; McCallum, J. S.; Kunng, F.- A. J. Am. Chem. Soc. 1988, 110, 7419.
4. Thermally stable acyloxy complexes of iron and ruthenium have recently been reported; see: Adams, H.; Maloney, C. A.; Muir, J. E.; Walters, S. J.; Winter, M. J. J. Chem. Soc., Chem. Commun. 1995, 1511.
5. For a few reactions of acyloxy-substituted chromium carbenes, see: (a) Murray, C. K.; Yang, D. C.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 5660. (b) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D.; Rogers, R. D. Organometallics 1990, 9, 3142.
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8. For a compilation of synthetic methods to prepare enol esters, see: Larock, R. C. Comprehensive Organic Transformations; VCH Publisher: New York, 1989; p 743. For some additional examples, see: (a) Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247. (b) Kowalski, C. J.; Haque, M. S. J. Am. Chem. Soc. 1986, 108, 1325. (c) Kikukawa, K.; Naritomi, M.; He, G.-X.; Wada, F.; Matsuda, T. J. Org. Chem. 1985, 50, 299. (d) Mitsudo, T.-a.; Hori, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1567.
9. For a compilation of synthetic methods to prepare enol esters, see: Larock, R. C. Comprehensive Organic Transformations; VCH Publisher: New York, 1989; p 743. For some additional examples, see: (a) Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247. (b) Kowalski, C. J.; Haque, M. S. J. Am. Chem. Soc. 1986, 108, 1325. (c) Kikukawa, K.; Naritomi, M.; He, G.-X.; Wada, F.; Matsuda, T. J. Org. Chem. 1985, 50, 299. (d) Mitsudo, T.-a.; Hori, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1567.
10. For a compilation of synthetic methods to prepare enol esters, see: Larock, R. C. Comprehensive Organic Transformations; VCH Publisher: New York, 1989; p 743. For some additional examples, see: (a) Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247. (b) Kowalski, C. J.; Haque, M. S. J. Am. Chem. Soc. 1986, 108, 1325. (c) Kikukawa, K.; Naritomi, M.; He, G.-X.; Wada, F.; Matsuda, T. J. Org. Chem. 1985, 50, 299. (d) Mitsudo, T.-a.; Hori, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1567.
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