Synthesis and Reactivity of some Aromatic Sulfides Substituted by an Ortho-Phosphonyl Group |
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Authors: | J Drabowicz S Masson C Mauger W Midura M Mikolajczyk J-F Saint-Clair |
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Institution: | 1. CMMS, Polish Academy of Sciences , Sienkiewicza 112, 90-363 , Lodz , Poland;2. LCMT, UMR CNRS 6507 ISMRA, Université , 14050 , Caen cedex , France |
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Abstract: | Abstract As phosphorus-based members of the biologically relevant thiosalicylic acid, monoesters of ortho-sulfinylated phenylphosphonic acids such as 3 and 4 (series a, R1=Me; b, R22-C6H4C02H) are of special interest. They might act both as potential sources of new anionic bidentate ligands for the synthesis of cisplatin analogues1] and as suitable precursors of phosphorus-containing endocyclic sulfoximides and hypervalent organo-sulfur species. We have therefore undertaken the synthesis of these compounds. The starting phenylphosphonic acid diisopropylesters 1 were formed by using a LDA-induced thiophosphate-mercaptophosphonate rearrangement2] described earlier and converted into their dimethyl counterpans 2 by means of a trans-silylation procedure followed by alkylation. We have now performed the selective half-hydrolysis of phosphonic acid diesters 1.2 and sulfoxidation of the resulting monoesters. |
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