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20.4.1.1.2.3 Variation 3: Using Phosphine-Based Reagents

DOI: 10.1055/sos-SD-020-00605

Keller, P. A.Science of Synthesis, (200720619.

The reaction of triphenylphosphine with benzoquinone derivatives 9 produces a violet complex 10, which can be used to promote the formation of anhydrides 11 from carboxylic acids in 5090% yields (Scheme 5).[‌18‌] Anhydrides produced by this method include mesitoic, benzoic, pivalic, and butyric anhydride. In a variation of this procedure, the use of tertiary phosphines and diphenylmercury, in the presence of carboxylic acids, also gives the anhydrides in 7480% yield.[‌19‌]

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