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- W2057158371 abstract "Substituted benzyloxychlorocarbenes (X-PhCH2OCCl) were generated photochemically at 25 degrees C in dichloroethane from appropriate diazirine precursors. Fragmentations of the carbenes produced were determined by laser flash photolysis. The data (X, kfrag in s-1) were: p-Me, 2.6 x 105; p-Ph, 8.3 x 104; H, 6.0 x 104; p-Cl, 5.2 x 104; m-Cl, 1.3 x 105; p-F3C, 2.1 x 106; p-O2N, 6.3 x 106. A Hammett correlation of log kfrag versus sigma+ was parabolic. The curvature was taken to imply the gradual change of the fragmentation mechanism from predominantly heterolytic for X-PhCH2CCl with electron-donating X (with developing positive charge on the benzylic carbon in the transition state) to predominantly homolytic for carbenes with electron-withdrawing X. This idea was supported by computational studies." @default.
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- W2057158371 date "2002-10-31" @default.
- W2057158371 modified "2023-09-30" @default.
- W2057158371 title "A Duality of Mechanisms for the Fragmentation of Substituted Benzyloxychlorocarbenes" @default.
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- W2057158371 doi "https://doi.org/10.1021/ja0207605" @default.
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