117831-78-4Relevant articles and documents
Fragmentation, Ring-opening, and Addition Reactions of Oxygen-conjugated Alkenyl Radicals derived by Rapid 1,5-Hydrogen Shifts in Vinyl Radicals. An Electron Spin Resonance and Kinetic Investigation
Gilbert, Bruce C.,Parry, David J.
, p. 875 - 886 (1988)
The addition od ether-derived oxygen-conjugated radicals .CR1R2OCHR1R2 to alkynes R3CCR4 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.