AI Article Synopsis
- Researchers synthesized unsymmetrical 9-chloro-9-phosphafluorenes and 9-chloro-9-arsafluorenes using thermolysis of m-terphenyldichlorophosphines and -arsines, achieving nearly 100% yield in just 5 minutes at temperatures of 200°C and 140°C, respectively.
- An alternative method involving an AlCl3-catalyzed Friedel-Crafts reaction at lower temperatures is available, but it is less efficient due to complicated workup processes.
- The new compounds were analyzed through various techniques, including NMR spectroscopy and mass spectrometry, highlighting their potential as good donor materials due to their ability to form complexes with
Article Abstract
Unsymmetrical 9-chloro-9-phosphafluorenes (dibenzophospholes) and 9-chloro-9-arsafluorenes (dibenzoarsoles) have been obtained by simple thermolysis of m-terphenyldichlorophosphines and -arsines in close to quantitative yields. The reaction temperatures are about 200 degrees C for the phosphines and 140 degrees C for the arsine, and the reactions are complete within 5 min. Alternatively, these compounds can be synthesized through an AlCl3-catalyzed Friedel-Crafts type ring-closure reaction at low temperatures, but this method suffers from difficult workup procedures. The P(As)-Cl functionality is readily alkylated. Methylation of m-xylyl derivative 4 afforded 1-(3,5-dimethylphenyl)-6,8,9-trimethyl-9-phosphafluorene, 11. The latter compound formed the complexes 11 x Fe(CO)4, 12, and 11 x RuCl2(eta(6)-p-cymene), 13, indicating its good donor properties. The new compounds have been characterized by 1H, 13C{1H}, and 31P{1H} NMR spectroscopy; mass spectrometry; and single-crystal X-ray crystallography in the case of 11, 12, and 13.
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| http://dx.doi.org/10.1021/ic051976l | DOI Listing |
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