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The first reaction product has been thought to involve a mercurinium ion (IV)183. suffered severe criticism. \ IVI 80-86 50 ELECTROPHILIC A D D I T I O N S T O U N S A T U R A T E D S Y S T E M S encourage trans addition, but in the few cases where the stereochemistry of the addition has been identified (norbornene and related compounds) it is predominantly cisla4. It may well be that two polar mechanisms can operate; in one, a four-centre transition state involving only the reagent and the olefin ( V ) would explain cis addition in sterically unfavourable environments, while the two-stage sequence involving a mercurinium ion or some kinetically equivalent species may be the more usual mode of reaction.

7 cis-n-5-Undecene. mole-I, ASt. 0 eu. Calculated for a second-order reaction; eqn. 21) is probably more appropriate. a ReJ'ercncm p p . RO-86 42 ELECTROPHILIC A D D I T I O N S TO U N S A T U R A T E D SYSTEMS 5. 1); in acidic media the epoxide may suffer ring-opening to yield the mono-ester of a glycol, reaction ( 5 . 2 P . 1) RCOZOH t Boeseken et first studied the kinetics of such reactions; the first report152dealt with the reaction of perbenzoic acid with derivatives of styrene in chloroform solution and despite the ease of decomposition of the reagent, styrene was proved to react less rapidly than p-methyl- or P-ethyl-styrene.

78 aq. aq. aq. aq. aq. aq. aq. aq. aq. ) Kinetic. 16) k("C) Solveti t Ref. 68 (10) aq . 159 (0) aq . 7 aq. 740 (0)" aq. S aq. 075 (25) aq. 4 aq. 067 (25) aq. 9 aq. 73)'q k," = 35(25) aq. 1 aq. 73)qq k, = 638 (0) aq . 8 X lo-' (25) aq. 273 (25) aq. 114 (25) aq. 8 (0) aq. 141 142 142 142 142 144 I45 144 145 144 145 143 146 146 146 147 Containing 10%. 20%. or 40% water. Containing sodium acetate to prevent acid-catalysed reaction. mole-'. LiCI-catalysed. mole-'. 0 kcal. 85. Relative to ethylene (competition rates).

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