Journal of the Chemical Society. Perkin transactions II p. 875 - 886 (1988)
Update date:2022-07-29
Topics:
Gilbert, Bruce C.
Parry, David J.
The addition od ether-derived oxygen-conjugated radicals .CR1R2OCHR1R2 to alkynes R3C<*>CR4 leads to vinyl radicals, most of which undergo a rapid 1,5-shift (k>105 s-1) to give radicals .CR1R2OCR1R2CR3=CHR4.The reactions of the latter species, as revealed by e.s.r. spectroscopy, include fragmentation (to give R1R2C=O and .CR1R2CR3=CHR4), ring-opening (e.g. for radicals from tetrahydrofuran and dioxane and their derivatives), and trapping via reaction with a further molecule of alkyne.A kinetic analysis is presented and results are interpreted in terms of the electronic and steric effects of substituents in the intermediates.
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