By C.H. Bamford
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Extra resources for Addition and Elimination Reactions of Aliphatic Compounds
Mole-';AS-t=-27eu. 083 (eqn. 2 1 ). mole-'. 1 truns-n-3-Undecene. 7 truns-n-4-Undecene. 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.
The earlier literature has been critically reviewed and assessed on this pointlW2. 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.
2 OZONE The detailed mechanism of the reaction of ozone with olefins proposed by involves initial attack upon the olefin to form a “primary Criegee et d15y ozonide” which suffers oxygen-oxygen and then carbon-carbon bond fission to form a reactive zwitterionic intermediate (111) which provides the “normal ozonide”, together with the products of rearrangement, polymerisation, or 5 A D D I T I O N O F O T H E R ELECTROPHILES secondary decomposition, viz. R~C=CR; - t 0, ---c RC-CR; \/ R,c-CR; I (Secondary o zon ide) I o+ -0-0 03 (Primary ozon ide) 45 m Rearrangement products Polymeric products R2C=0 t H202 Such a sequence explains, for instance, the formation of the same secondary ozonide from cis or trans-stilbene'", and the isolation of the secondary ozonide of isobutene from the ozonolysis of 2,3-dimethyl-2-butene in the presence of formaldehyde1s9,viz.