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The quinonoid analogues of TTF are better electron donors than TTF itself. Their prototype 4 has now been synthesized for the first time. Wittig–Horner reaction of the dithiol derivative 1 with the cyclopentadiene adduct of benzoquinone, 2, gives 3, which undergoes retro-Diets–Alder reaction to yield 4 as dark red crystals. TTF undergoes oxidation at + 0.28 and + 0.64 V (vs. SCE), whereas 1 is oxidized at −0.11 and −0.04 V (vs. SCE).
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Yamashita et al. (1989) studied this question.
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