Hydrogenation of alkynes with hydrated nickel chloride, lithium and a catalytic amount of naphthalene

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 149-152

  Alonso, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0031013933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02239-3     Document Type: Article

References (27)

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13. tOH, see: Whitesides, G. M.; Ehmann, W. J. J. Org. Chem. 1970, 35, 3565-3567.
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15. (a) For the first account on this reaction, see: Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
16. (b) For a review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
17. For a review on functionalised organolithium compounds, see: Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
18. For the last paper from our laboratory on this topic, see: (a) Huerta, F. F.; Gómez, C.; Yus, M. Tetrahedron 1996, 52, 13243-13254.
19. (b) Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1996, 52, 8545-8564.
20. (c)Guijarro, A.; Yus, M. Tetrahedron 1996, 52, 1797-1810.
21. Alonso, F.; Yus, M. Tetrahedron Lett. 1996, 37, 6925-6928.
22. 2O as the nickel salt: after ca. 1 h PhCD=CDPh was detected by GLC-MS.
23. 13C NMR), obtained by Lindlar-catalysed hydrogenation of 4-octyne (Lindlar, H.; Dubois, R. Org. Synth. Coll. Vol. V.; Baumgarten, H. E., Ed.; J. Wiley & Sons: New York, 1973; pp. 880-883).
24. A mixture of Z-(60%) and E-4-octene (20%) together with 2-octenes (16%) and other octenes (4%) was obtained (GLC-MS analysis).
25. 3,4 = 16.2 Hz.
26. Guijarro, A.; Yus, M. Tetrahedron 1995, 51, 231-234.
27. 2,4 = 1.85 Hz) prepared following the procedure described in ref 14.