Synthesis of conjugated diallenes by double [2,3]-sigmatropic rearrangement of conjugated diyne trichloromethanesulfenates

Synthetic Communications

Volumn 29, Issue 15, 1999, Pages 2629-2637

  Raj, C Paul ^a   Braverman, S ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; SULFENIC ACID DERIVATIVE;

ARTICLE; CONJUGATION; ESTERIFICATION; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS;

EID: 0033062195     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908086424     Document Type: Article

References (22)

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3. Schuster, H. F, and Coppola, G. M., "Allenes in Organic Synthesis," John Wiley & Sons, 1984; Claesson, A. and Olsson, L. I., "Allenic Intermediates in Organic Synthesis," in "The Chemistry of the Allenes," Landor, S. R., Ed., Academic press, London, vol. 3, pp. 735-773.
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5. Landor, P. D., "Synthesis of Conjugated Allenes," in The Chemistry of the Allenes, Landor, S. R., Ed., Academic press, London, vol. 1, pp. 207-227; Hopf, H. Angew Chem. Int. Ed. Engl., 1970, 9, 732; Chem. Ber., 1971, 104, 1499.
6. Landor, P. D., "Synthesis of Conjugated Allenes," in The Chemistry of the Allenes, Landor, S. R., Ed., Academic press, London, vol. 1, pp. 207-227; Hopf, H. Angew Chem. Int. Ed. Engl., 1970, 9, 732; Chem. Ber., 1971, 104, 1499.
7. Braverman, S. and Segev, D., J. Am. Chem. Soc., 1974, 96, 1245.
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9. Braverman, S., Duar, Y. and Segev, D., Tetrahedron Lett., 1976, 3181; Braverman, S. and Duar, Y., Tetrahedron Lett., 1978, 1493; Braverman, S., and Freund, M., Tetrahedron, 1990, 46, 5759; Braverman, S. and Duar, Y., J. Am. Chem. Soc., 1990, 112, 5830; Braverman, S., Phosphorous and Sulfur, 1985, 23, 297.
10. Braverman, S., Duar, Y. and Segev, D., Tetrahedron Lett., 1976, 3181; Braverman, S. and Duar, Y., Tetrahedron Lett., 1978, 1493; Braverman, S., and Freund, M., Tetrahedron, 1990, 46, 5759; Braverman, S. and Duar, Y., J. Am. Chem. Soc., 1990, 112, 5830; Braverman, S., Phosphorous and Sulfur, 1985, 23, 297.
11. Braverman, S., Duar, Y. and Segev, D., Tetrahedron Lett., 1976, 3181; Braverman, S. and Duar, Y., Tetrahedron Lett., 1978, 1493; Braverman, S., and Freund, M., Tetrahedron, 1990, 46, 5759; Braverman, S. and Duar, Y., J. Am. Chem. Soc., 1990, 112, 5830; Braverman, S., Phosphorous and Sulfur, 1985, 23, 297.
12. Braverman, S., Duar, Y. and Segev, D., Tetrahedron Lett., 1976, 3181; Braverman, S. and Duar, Y., Tetrahedron Lett., 1978, 1493; Braverman, S., and Freund, M., Tetrahedron, 1990, 46, 5759; Braverman, S. and Duar, Y., J. Am. Chem. Soc., 1990, 112, 5830; Braverman, S., Phosphorous and Sulfur, 1985, 23, 297.
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15. Toda, F. and Takehira, Y., J. Chem. Soc., Chem. Commun., 1975, 174 and references cited therein.
16. Hopf, H., Chem. Ber., 1971, 104, 3087.
17. Hassner, A. and Stumer, C., "Organic Synthesis Based on Name Reactions and Unnamed Reactions," Pergamon press, Oxford, 1994, p. 266.
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20. eg., Okamura, W. H., Shen, G.-Y. and Tapia, R., J. Am. Chem. Soc., 1986, 108, 5018 and previous references cited therein; for a review on rearrangements of allenes in general, see Braverman, S. in "Chemistry of Double-Bonded Functional Groups," Patai, S., Ed., Wiley, Chichester, 1989, Supplement A2, pp. 963-1060.
21. eg., Okamura, W. H., Shen, G.-Y. and Tapia, R., J. Am. Chem. Soc., 1986, 108, 5018 and previous references cited therein; for a review on rearrangements of allenes in general, see Braverman, S. in "Chemistry of Double-Bonded Functional Groups," Patai, S., Ed., Wiley, Chichester, 1989, Supplement A2, pp. 963-1060.
22. Fieser, L. F. and Williamson, K. L., "Organic Experiments," D. C. Heath and Company, Sixth Ed., New York, 1987, pp. 358-360.