Mechanism of dehydrobromination of 1, 2-dibromo-1-phenylethane under conditions of phase-transfer catalysis

VV Suvorova, LP Panicheva, YV Mamontova…

Index: Suvorova; Panicheva; Mamontova; Belyatskii Russian Journal of Organic Chemistry, 2003 , vol. 39, # 7 p. 957 - 962

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Abstract

Abstract Selective dehydrobromination of 1, 2-dibromo-1-phenylethane to α-bromostyrene was effected under conditions of phase-transfer catalysis in systems containing KOH, toluene, and tetraalkylammonium bromides. The high selectivity of the catalytic systems originates from stabilization by lipophilic cation of the phase-transfer catalyst of a E1cb-like transition state in the E2 mechanism. In the presence of a catalytic amount of lipophilic ...

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