Tetrahedron p. 4987 - 4994 (1985)
Update date:2022-07-29
Topics:
Tomoika, H.
Ozaki, Y.
Izawa, Y
The solvent effect on the reactivity of singlet carbenes has been investigated.Competition reactions between pairs of alcohols for arylcarbenes in various solvents indicates that the O-H insertion selectivity is influenced only by 1,4-dioxane.Thus, phenylcarbene is some 33 times more reactive toward methanol relative to t-butyl alcohol in 90 molpercent dioxane than without solvent.Similar competition reactions between alcohol and olefin indicate that the O-H insertion-addition selectivities of arylcarbenes are considerably altered by dioxane.These results are interpreted as indicating that dioxane stabilizes singlet carbenes by complexing with its ione pairs of electrons.
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