Tetrahedron

Competitive acylation of arylstyrylsilanes: Controlling silanucleophile reactivity

MA Brook, C Henry

Index: Brook, Michael A.; Henry, Courtney Tetrahedron, 1996 , vol. 52, # 3 p. 861 - 868

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Citation Number: 9

Abstract

Electrophilic substitution reactions occurred cleanly between acyl cations and arylstyrylsilanes 2–4. With an unsubstituted aryl group, 2 underwent transfer of the styryl group to form styryl ketone 5 as would be predicted from previous kinetic studies. With increasing methyl group substitution of the aryl group, aryl group transfer occurred competitively such that 3 showed a 2: 1 preference for destyrylation: dearylation giving 10: ...

~85%

~61%

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Competitive acylation of arylstyrylsilanes: Controlling sila...

[Tetrahedron, , vol. 52, # 3 p. 861 - 868]