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Volumn 119, Issue 19, 1997, Pages 4424-4431

Titanocene-catalyzed cyclocarbonylation of o-allyl aryl ketones to γ- butyrolactones

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; LACTONE DERIVATIVE; TITANOCENE;

EID: 0030946106     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970115b     Document Type: Article
Times cited : (95)

References (58)
  • 1
    • 0027658856 scopus 로고
    • For lead references, see: (a) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. (b) Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 3.7, p 323. (c) Buchwald, S. L.; Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 7.4, p 771 and references within.
    • (1993) Science , vol.261 , pp. 1696
    • Broene, R.D.1    Buchwald, S.L.2
  • 2
    • 0027658856 scopus 로고
    • Hegedus, L. S., Ed.; Pergamon: Oxford, Chapter 3.7
    • For lead references, see: (a) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. (b) Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 3.7, p 323. (c) Buchwald, S. L.; Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 7.4, p 771 and references within.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 323
    • Broene, R.D.1
  • 3
    • 0027658856 scopus 로고
    • Hegedus, L. S., Ed.; Pergamon: Oxford, Chapter 7.4, and references within
    • For lead references, see: (a) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. (b) Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 3.7, p 323. (c) Buchwald, S. L.; Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol.12, Chapter 7.4, p 771 and references within.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 771
    • Buchwald, S.L.1    Broene, R.D.2
  • 4
  • 5
    • 0001136410 scopus 로고
    • Hegedus, L. S., Ed.; Pergamon: Kidlington, and references within
    • Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Kidlington, 1995; Vol. 12, p 703 and references within.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703
    • Schore, N.E.1
  • 6
    • 0001069332 scopus 로고
    • For catalytic examples, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. (c) Pagenkopf, B. L.; Livinghouse, T. J. J. Am. Chem. Soc. 1996, 118, 2285.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3159
    • Jeong, N.1    Hwang, S.H.2    Lee, Y.3    Chung, Y.K.4
  • 7
    • 85022624758 scopus 로고
    • For catalytic examples, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. (c) Pagenkopf, B. L.; Livinghouse, T. J. J. Am. Chem. Soc. 1996, 118, 2285.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8793
    • Lee, B.Y.1    Chung, Y.K.2    Jeong, N.3    Lee, Y.4    Hwang, S.H.5
  • 8
    • 0029871213 scopus 로고    scopus 로고
    • For catalytic examples, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. (c) Pagenkopf, B. L.; Livinghouse, T. J. J. Am. Chem. Soc. 1996, 118, 2285.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2285
    • Pagenkopf, B.L.1    Livinghouse, T.J.2
  • 17
    • 0000443799 scopus 로고
    • Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford
    • Negishi, E.-i. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 1163-1184.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1163-1184
    • Negishi, E.-I.1
  • 22
    • 14444268253 scopus 로고    scopus 로고
    • note
    • The metallacycles in many cases are formed initially as kinetic mixtures of diastereomers which then equilibrate to the thermodynamically favored product. Equilibration is slow at lower temperatures. (See ref 7)
  • 29
    • 14444270319 scopus 로고    scopus 로고
    • note
    • 3: 65% conversion.
    • , vol.24
  • 30
    • 0010811362 scopus 로고
    • Angelici, R. J., Ed.; John Wiley and Sons, Inc.: New York
    • Titanocene dicarbonyl is available from Strem or is easily prepared: Sikora, D. J.; Moriarty, K. J.; Rausch, M. D. In Inorganic Synthesis; Angelici, R. J., Ed.; John Wiley and Sons, Inc.: New York, 1990; Vol. 28, p 248.
    • (1990) Inorganic Synthesis , vol.28 , pp. 248
    • Sikora, D.J.1    Moriarty, K.J.2    Rausch, M.D.3
  • 31
    • 14444287469 scopus 로고    scopus 로고
    • note
    • 3: 50% conversion.
  • 33
    • 0003301099 scopus 로고
    • 2 to form fulvenes with concommitant destruction of the titanocene framework: Gleiter, R.; Wittwer, W. Chem. Ber. 1994, 127, 1797.
    • (1994) Chem. Ber. , vol.127 , pp. 1797
    • Gleiter, R.1    Wittwer, W.2
  • 38
    • 0042480239 scopus 로고
    • For some examples of aromatic ketones acting as electron acceptors in charge transfer reactions, see: (a) Ashby, E. C.; Goel, A. B.; Argyropoulos, J. N. Tetrahedron Lett. 1982, 23, 2273. (b) Ashby, E. C.; Argyropoulos, J. N. J. Org. Chem. 1986, 51, 472. (c) Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1994, 116, 1994.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2273
    • Ashby, E.C.1    Goel, A.B.2    Argyropoulos, J.N.3
  • 39
    • 0042477109 scopus 로고
    • For some examples of aromatic ketones acting as electron acceptors in charge transfer reactions, see: (a) Ashby, E. C.; Goel, A. B.; Argyropoulos, J. N. Tetrahedron Lett. 1982, 23, 2273. (b) Ashby, E. C.; Argyropoulos, J. N. J. Org. Chem. 1986, 51, 472. (c) Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1994, 116, 1994.
    • (1986) J. Org. Chem. , vol.51 , pp. 472
    • Ashby, E.C.1    Argyropoulos, J.N.2
  • 40
    • 0042480239 scopus 로고
    • For some examples of aromatic ketones acting as electron acceptors in charge transfer reactions, see: (a) Ashby, E. C.; Goel, A. B.; Argyropoulos, J. N. Tetrahedron Lett. 1982, 23, 2273. (b) Ashby, E. C.; Argyropoulos, J. N. J. Org. Chem. 1986, 51, 472. (c) Fukuzumi, S.; Okamoto, T. J. Am. Chem. Soc. 1994, 116, 1994.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1994
    • Fukuzumi, S.1    Okamoto, T.2
  • 42
    • 0040836309 scopus 로고
    • For a review on electron transfer induced substitution reactions on metal carbonyl complexes, see: Albers, M. O.; Coville, N. J. Coord. Chem. Rev. 1984, 53, 227.
    • (1984) J. Coord. Chem. Rev. , vol.53 , pp. 227
    • Albers, M.O.1    Coville, N.2
  • 50
    • 0010811362 scopus 로고
    • Angelici, R. J., Ed.; John Wiley and Sons, Inc.: New York
    • Sikora, D. J.; Moriarty, K. J.; Rausch, M. C. In Inorganic Synthesis; Angelici, R. J., Ed.; John Wiley and Sons, Inc.: New York, 1990; Vol. 28, p 248.
    • (1990) Inorganic Synthesis , vol.28 , pp. 248
    • Sikora, D.J.1    Moriarty, K.J.2    Rausch, M.C.3


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