A novel copper(II)/tin(II) reagent for regio- and chemoselective carbonyl propargylation

Organometallics

Volumn 18, Issue 15, 1999, Pages 2782-2785

  Kundu, Abhijit ^a   Prabhakar, Sripadi ^a   Vairamani, M ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000549624     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9900317     Document Type: Article

References (31)

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2. For review see: (a) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 2, pp 81-98. (b) Panek, J. S. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 1, p 595 and references therein.
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16. Imai et al. showed one example of the reaction of benzaldehyde with propargyl bromide in the presence of stannous chloride, cuprous bromide, and 30% aqueous ammonium fluoride resulting in a mixture of homopropargyl and homoallenyl alcohols (96:4, 61% isolated yield): Imai, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1994, 277.
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21. Extended refluxing for 48 h causes significant decomposition leading to a messy mixture of unidentified products.
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25. Stannous bromide was chosen in this study to overcome the complicacy due to halo exchange as observed in earlier investigation on carbonyl allylation studies: see ref 5.
26. For NMR of allenyl and propargyl stannanes, see refs 9 and 4b.
27. Curiously, a similar experiment but in the absence of stannous halide after 24 h showed the formation of allenyl bromide. This is in accordance with earlier observation: Jacobs, T. L.; Petty, W. L. J. Org. Chem. 1963, 28, 1360.
28. For organostannanes, EIMS is a more effective probe than FABMS: Harrison, P. G. Chemistry of Tin; Blackie: London, 1989; p 105.
29. Metastable ion spectra can be used for structure elucidation. In this technique, the ion under study is selected and collided with a neutral gas, usually helium, to induce the decomposition of the ion. This leads to fragment ions formed exclusively from the selected ion. The resulting spectrum is called "mass-analyzed ion kinetic energy - collision-induced dissociation" or MIKE-CID spectrum: Chapman, J. R. Practical Organic Mass Spectrometry, 2nd ed.; John Wiley: New York, 1995; p 235.
30. Cu(II) salts are easily reduced by Sn(II) halides: Nunes, T. L. Inorg. Chem. 1970, 9, 1325.
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