The reactions of the 1,4-bisphosphoniumsalt (1) withquinones (4), (8), (14), and (25), in the presence of lithium hydroxide did not afford bis-Wittig products, with exception of compound (6). The quinone (4) in addition to compound (6) gave the o-quinomethane derivative (7), quinone (14) gave compounds (17), (18), and (19), via a simple Wittig reaction, followed by Michael addition of a second ylide species, while quinone (25) gave the 1,3-benzodioxole (26). A deviation of the typical Wittig procedure can account for the formation of compound (12) from the quinone (8). The reaction of the 1,4-bisphosphonium salt (20) with the dione (14) is also described. Significant hydrolysis of the formed ylide groups was observed in all reactions.
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Nicolaides et al. (1986) studied this question.