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• W1901490694 abstract "Abstract The diesters ( E )‐RO 2 CCH=CHCO 2 R [R = Et, CH 2 Ph, i Pr, i Bu, t Bu, 2‐ethylhexyl, (–)‐menthyl, (–)‐bornyl] undergo 1,4‐trichloromethylation with Me 3 SiCCl 3 in 84–95 % yield with Bu 4 NX (X = OAc, Cl, F; 0.5–10 mol‐%) as an initiator. Optimal catalysis is attained with X = OAc and F; chloride is less effective, bromide is inadequate. Poor regioselectivity but high yields are demonstrated by mixed diesters (2 examples, both > 80 %). Heating of the trichloromethyl adducts, in the presence of Bu 4 N(OAc), leads to equilibrating, approximately equimolar, mixtures of RO 2 CC(=CCl 2 )CHCO 2 R and RO 2 CCH=CClCHClCO 2 R above 100 °C (7 examples). The latter component is produced under thermodynamic control, which can be isolated pure in some cases. The former is the kinetic product of E2 elimination." @default.
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• W1901490694 date "2015-08-06" @default.
• W1901490694 modified "2023-10-16" @default.
• W1901490694 title "1,4-Addition of TMSCCl₃to (<i>E</i>)-Fumaric Esters and Thermal Rearrangement of the Adducts to 3,4-Dichloropent-2-enedioates" @default.
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• W1901490694 doi "https://doi.org/10.1002/ejoc.201500730" @default.
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