The acid-catalyzed demetalation of 1-(tri-n-butylstannyl)-2-phenylethyn. A surprisingly small β-stannyl effect

Canadian Journal of Chemistry

Volumn 74, Issue 7, 1996, Pages 1366-1368

  Egle, I ^a   Gabelica, V ^a   Kresge, A J ^a   Tidwell, T T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Carbocation stabilization; Protodemetalation; silyl effect; stannyl effect

Indexed keywords

ACETONITRILE; AROMATIC COMPOUNDS; ION EXCHANGE; ISOTOPES; ORGANIC ACIDS; PROTONS; SILICON COMPOUNDS; SPECTROMETERS;

BETA STANNYL EFFECT; CARBOCATION STABILIZATION; HYDRONIUM ION RATE CONSTANT; PERCHLORIC ACID; PROTODEMETALATION; PROTONATION; ULTRASONIC BATH; VINYL CARBOCATION;

REACTION KINETICS;

EID: 0030193011     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-153     Document Type: Article

References (9)

1. J.B. Lambert. Tetrahedron, 46, 2677 (1988); Y. Apeloig. In The chemistry of organic silicon compounds. Edited by Z. Rappoport. Wiley, New York. 1989. p. 57.
2. J.B. Lambert. Tetrahedron, 46, 2677 (1988); Y. Apeloig. In The chemistry of organic silicon compounds. Edited by Z. Rappoport. Wiley, New York. 1989. p. 57.
3. J.B. Lambert, G.-t. Wang, and D.H. Teramura. J. Org. Chem. 53, 5422 (1988).
4. C. Dallaire and M.A. Brook. Organometallics, 12, 2332 (1993).
5. M.W. Logue and K. Teng. J. Org. Chem. 47, 2549 (1982).
6. A.J. Kresge, R.A. More O'Ferrall, and M.F. Powell. In Isotopes in organic chemistry. Edited by E. Buncel and C.C. Lee. Elsevier, New York. 1987. Chap. 4.
7. N. Banait, M. Hojatti, P. Findlay, and A.J. Kresge. Can. J. Chem. 65, 441 (1987).
8. A.J. Kresge and J.B. Tobin. Angew. Chem. Int. Ed. Engl. 32, 721 (1993).
9. V. Gabelica and A.J. Kresge. J. Am. Chem. Soc. 118, 3838 (1996).