Chlorine -elimination of a diaryl-1,2-dichloroethylene with base

Aromatic and Alkaromatic Chlorocarbons

“…(4) A 92% yield of PTM is obtained by oxidation of tetraethylammonium perchlorotriphenylmethide (CLXXXVII) with iodine (Section 1.10.3) [345,346]. (5) 4-Bromo-(CLXXXIII; Section 1.8.2i) and 4-iodotetradecachlorotriphenylmethyl (CLXXXIX; Section 1.8.2h) radicals react with chlorine in carbon tetrachloride in the dark to give PTM, the yields being 91 and 98.5%, respectively [347]. These reactions are summarized in the diagram on page 137.…”

“…These reactions are described in some detail in the corresponding sections. PTM reacts with a boiling solution of hydrogen iodide in acetic acid furnishing the aH-compound (CLXXXIV) [318,347]. This is probably an electron transfer concerted with, or followed by, a proton transfer rather than a direct hydrogen atom extraction from hydrogen iodide (cf.…”

“…Treatment of the methyl ester (CC) (Section 1.9) with reagent BCR (Section 1.8.1a) at room temperature, followed by oxidation with iodine gives the title radical (CCI) in 85.4% yield [347]. Methylation of the acid radical (CCII) (Section 1.8.2h) with diazomethane in ethyl ether [347] gives a better yield (94.7%).…”

“…Methylation of the acid radical (CCII) (Section 1.8.2h) with diazomethane in ethyl ether [347] gives a better yield (94.7%).…”

“…It is soluble in chlorinated solvents and its infrared, ultraviolet-visible, and epr spectra have been taken [347] . In stability tests it behaves much like PTM.…”