Abstract
The distribution of products formed in the oxidation by Tl(N03)3 of the olefins RCH=CH2 and R1R2C=CH2 in methanol has been studied. The monosubstituted ethylenes (R = alkyl) lead to a diether RCH(OCH3)—CH2OCH3 and to a ketone RC(O)CH3, the latter being formed in an amount of 40–55%; when R=CH2Cl only the diether is formed. With the disubstituted ethylenes R1R2C=CH2, the ratio of the rate constants for the formation of the isomeric ketones k1 (implying the migration of R1) and k2 (implying the migration of R2) is related to the polar Taft constants by the equation log (k2lk1) = ρ*(σ2* − σ1*) with ρ* = −4. This indicates that the migration of the better electron donor occurs preferentially. In addition to the ketone mixture (∼10–15%), ∼75–80% of the diether and ∼10–20% of the aldehyde are formed. [Journal translation]
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