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- W2018223469 abstract "When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n-butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The E/Z ratio seems to depend on the amount of the base used and the phosphonium salt involved.Key words: phosphonium salts, homocoupling, 1,2-diarylalkene, Ylids." @default.
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- W2018223469 date "2008-07-01" @default.
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- W2018223469 title "Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents" @default.
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- W2018223469 doi "https://doi.org/10.1139/v08-056" @default.
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