Journal of the Chemical Society. Perkin transactions II p. 1233 - 1240 (1986)
Update date:2022-08-29
Topics:
Liu, Michael T. H.
Subramanian, Ramasamy
The insertion reaction of the para-substituted benzylchlorocarbenes with methanol shows a second-order dependence in methanol, but only a first-order dependence in ethylene glycol.The results are consistent with a mechanism whereby the carbene inserts into the O-H bond of the alcohol dimer or oligomer by electrophilic attack of the carbene on the oxigenone pair to produce a reversibly formed ylide intermediate.The effects of the substituents indicate that electron-releasing group favours rearrangement while electron-withdrawing group facilitates insertion.Photolysis of halogenodiazirines in methanol at low temperatures give rise to V-shaped Arrhenius behaviour and the importance of N2 in influencing the reactivity of the singlet halogenocarbene in the matrix is demonstrated.
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