A convenient synthesis of a-tributylstannyl esters

Synthetic Communications

Volumn 14, Issue 1, 1984, Pages 27-32

  Zapata, Antonio ^a   Carola, Acuña A ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84951387347     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397918408060860     Document Type: Article

References (10)

1. Lutsenko, I. F., Baukov, Y. I. and Burlachenko, G. S., J. Organometal. Chem., 1966, 6, 496, and references cited therein.
2. Lesbre, M. and Buisson, R., Bull. Soc. Chim. France, 1957,1204.
3. Rathke, M. W. and Sullivan, D. F., J. Am. Chem. Soc., 1973, 95, 3050.
4. Olofson, R. A. and Dougherty, C. M., J. Am. Chem. Soc., 1973, 95, 582.
5. Addition of tributyltin chloride to the ester enolate obtained from lithium dicyclohexylamide and ethyl isobutyrate, followed by a non-aqueous work-up, gave only the C-stannylated product. In contrast, silylation of the same ester enolate is known to give 99% of the O-silylated product.
6. Rathke, M. W. and Sullivan, D. F., Synth. Commun., 1973, 2, 67.
7. Meganem, F., Besace, Y. and Lequan, M., Synthesis, 1977, 310.
8. Some a-stannyl esters can be prepared by addition of tributylstannane to 3, 3-disubstituted acrylates
9. Pereyre, M., Colin, G. and Valade, J., C. R. Acad. Sci., Ser. C,1967, 264, 1204.
10. 1H NMR spectra were taken in deuterated chloroform using tetramethylsilane as internal standard. IR spectra were taken neat. 1: 1H NMR&1.83 (s, 2H), 1.4 (s, 9H), 1, 8 - 0.7 (m, 27H); IR 1690 cm-1. 2:lH NMR 6 4.05 (q, 2H), 1.92 (s, 2H), 1.8-0.7 (m, 30H); IR 1700 cm-1. 3: 1H NMR 6 3.6 (s, 3H), 1.9 (s, 2H), 1.8-0.7 (m, 27H); IR 1720 cm-1. 4: 1H NMR 6 4.1 Xq, 2H), 2.4 (q, 1H), 1, 8 - 0.7 (m, 33H); IR 1700 cm-1. 5: 1H NMR 6 4.1 (q, 2H), 1.4 (s, 6H), 1.8-0.7 (m, 30H); IR 1700 cm-16: 1H NMR 6 3.6 (s,3H), 1.4 (s,6H), 1.8-0.7 (m,27H); IR 1700 cm-1. 7: 1H NMR 6 4.1 (q,2H), 2.3 (m,1H), 1.8-0.7 (m,41H); IR 1700 cm-1