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A Mechanistic Study of the Acid- and Base-catalysed Cleavages of β-Trimethylstannylstyrenes by Abbas Alvanipour; Colin Eaborn; David R.M. Walton is a Chemistry article available to read on EtoBox.

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The cleavages of cis-and tram-PhCH=CHSnMe3 in l/10 AcOD-MeOD have been shown to give cis-and tnzns-PhCH=CHD, respectively. The rates of cleavage of some XCJ!&CH=CHSnMe, compounds in l/10 AcOH-MeOH at 50°C have been measured; there is no significant difference between the rates for cisand trans-PhCH=CHSnMe,, and the relative rates of cleavage as X is varied are (X = H), l.O;p-OMe, 7.0;p-Me, 2.3; m-Cl, 0.34; m-Br, 0.36. There is an excellent correlation with (T+ constants, with a p value of 1.1. The results are interpreted in terms of rate-determining proton transfer to the P-carbon atoms, and it is suggested that acid cleavages of vinyl-HgX bonds involve analogous mechanisms. PhSnMe, is cleaved 20 times as slowly as PhCH=CHSnMe, 'm the l/10 AcOH/MeOH. The rates of cleavage of XC,H\_,CH=CHSnMe, compounds by a mixture of MeOH (3 vol.) and 2 M aqueous NaOH (2 vol.) have been measured; trans-PhCH=CHSnMe, is cleaved about 1.3 times as rapidly as its cis-isomer, and about 12 times as rapidly as a mixture of cis-and trans-PhCH=CHSnEt,. The relative rates for the various XC6H,CH=CHSnMe, compounds (mainly transisomers) are (X =) H, l.O;pOMe, O.SS;p-Me, 0.92; m-Cl,: 1.67; nr-Br, 1.65. Cleavag

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Author

Abbas Alvanipour; Colin Eaborn; David R.M. Walton

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1980

Language

EN

Field

Chemistry (Physical Sciences)