Fine Tuning the Si-Sn Bond: Transmetalations Forming Either Trialkylstannyl or Trialkylsilyl Higher Order Cyanocuprates

Journal of Organic Chemistry

Volumn 54, Issue 21, 1989, Pages 4975-4977

  Lipshutz, Bruce H ^a   Reuter, Deborah C ^a   Ellsworth, Edmund L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006600741     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00282a001     Document Type: Article

References (9)

1. Organotin Compounds in Organic Synthesis; Tetrahedron Sym-posia-in-Print Number 36; Yamamoto, Y., Ed.; 1989. Pereyre, M.; Quintard, J. P. ; Rahm, A. In Tin in Organic Synthesis; Butterworths: London, 1987.
2. Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett., in press, Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. J. Org. Chem. 1989, 30, 2065. Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988,110, 2641.
3. Piers, E.; Tillyer, R. D. J. Org. Chem. 1988, 53, 5366. Gilbertson, S. R.; Challlener, C. A.; Bos, M. E.; Wulff, W. D. Tetrahedron Lett. 1988, 29, 4795.
4. Chernard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. Tamborski, P. C.; Ford, F. E.; Soloski, E. J. J. Org. Chem. 1963, 28, 237. The purity of 2, prepared from addition of n-Bu3SnH to LDA which contained excess TMS-C1 at -78 °C, is highly variable with n-Bi4Sn being the major contaminant. Thus, excess 2 was used to form 4, the amount being determined by GC analysis of 2. For the recent preparation of Bu3SnSiMe2Ph and MesSnSiMe2Ph, see: Ritter, K. Synthesis 1989, 218.
5. Chenard, B. L.; Laganis, E. D.; Davidson, F.; Rajan Babu, T. V. J. Org. Chem. 1985, 50. 3666.
6. Prepared as described by Chenard4ausing ClSiMe2(thexyl) in place of CiSiMe2(t-Bu); bp 110 °C (23 mmHg.)
7. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836. See also ref 4b.
8. Previously observed with PhMe2Si(Me)Cu(CN)Li2; cf. Fleming, I.; Newton, T. W. J. Chem. Soc., Perkin Trans. 1 1984, 1805.
9. Lipshutz, B. H. Synthesis 1987, 325 and references therein.