Addition to Electron Deficient Olefins of α-Oxy Carbon- Centered Radicals, Generated from Cyclic Ethers and Acetals by the Reaction with Alkylperoxy- λ3-iodane
作者:T. Sueda、Y. Takeuchi、T. Suefuji、M. Ochiai
DOI:10.3390/10010195
日期:——
Thermal decomposition of 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one in cyclic ethers and acetals at 50 degrees C generates alpha-oxy carbon-centered radicals, which undergo an addition reaction with vinyl sulfones and unsaturated esters.
Oxygen Promoted Addition of 1,3-Dioxolane to Electron-deficient Alkenes
作者:Yoshihisa Watanabe、Yasushi Tsuji、Ryo Takeuchi
DOI:10.1246/bcsj.56.1428
日期:1983.5
1,3-Dioxolane reacted with electron-deficient alkenes, such as diethyl maleate, maleic anhydride, diethyl fumarate and fumaronitrile, under an oxygen atmosphere or in air to give 1:1 adducts in good to excellent yields. The presence of oxygen promoted the reaction. The reaction appears to be characteristic of 1,3-dioxolane. Methylal and ethylal did not react with diethyl maleate under the same conditions
Radical addition of aldehydes and masked aldehydes like 1,3-dioxolanes to electron-deficient alkenes was achieved by the use of catalytic amounts of BPO and N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst under mild conditions. Three-component radical coupling of 1,3-dioxolanes, maleates, and alkenes was performed in the presence of BPO and NHPI under similar conditions. (C) 2003 Elsevier Ltd. All rights reserved.