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Synlett 1999; 1999(6): 822-824
DOI: 10.1055/s-1999-2706
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New Feature of Friedel-Crafts Phosphonation of Anisoles: Unexpected In Situ Methylphosphorylation Reaction

Graziano Baccolini* , Carla Boga
  • *Dipartimento di Chimica Organica "A. Mangini", Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy; Fax +39 (51) 6 44 36 54; E-mail: baccolin@ms.fci.unibo.it
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Publication Date:
31 December 1999 (online)

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Anisoles 1, reacting with AlCl3 and PCl3 with appropriate reagent ratios, give, in good yields, the corresponding diaryl methylphosphonates 2 or the methylphosphinates 3b,c and the methylphosphine oxides 4b,c. This unexpected in situ methylphosphorylation explains the reported limited and conflicting results to obtain methoxy-substituted arylphosphonous dichloride with the same reagents. A suggested mechanism is also reported.

anisoles - Friedel-Crafts reactions - phosphorylation - phosphorus compounds - phosphorus trichloride

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