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Phosphoric and phosphinic sulfonic anhydrides – reinvestigation and corrections. Novel methods of synthesis

1982; Wiley; Volume: 115; Issue: 4 Linguagem: Inglês

10.1002/cber.19821150438

0009-2940

Wojciech Da̧bkowski, Jan Michalski, Czeslaw Radziejewski, Zbigniew Skrzypczyński,

Asymmetric Hydrogenation and Catalysis

Chemische BerichteVolume 115, Issue 4 p. 1636-1643 Organic Chemistry Phosphoric and phosphinic sulfonic anhydrides – reinvestigation and corrections. Novel methods of synthesis Wojciech Dabkowski, Wojciech Dabkowski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorJan Michalski, Corresponding Author Jan Michalski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandCentre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorCzeslaw Radziejewski, Czeslaw Radziejewski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorZbigniew Skrzypczyński, Zbigniew Skrzypczyński Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this author Wojciech Dabkowski, Wojciech Dabkowski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorJan Michalski, Corresponding Author Jan Michalski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandCentre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorCzeslaw Radziejewski, Czeslaw Radziejewski Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this authorZbigniew Skrzypczyński, Zbigniew Skrzypczyński Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Boczna 5, 90–362 Lodz, PolandSearch for more papers by this author First published: April 1982 https://doi.org/10.1002/cber.19821150438Citations: 19AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstracten Earlier works from this and other laboratories on phosphoric and phosphinic sulfonic anhydrides have been reinvestigated. It was found that no single reaction described in the past provides a general method for the production of mixed anhydrides RR′P(O)SO2R″ (3) in high yields of isolated products. The following three efficient synthetic procedures leading to pure anhydrides 3 are described: a) Trifluoromethanesulfonic acid promoted reaction of phosphinic acid 9 with sulfonic triazolides 10. b) Reaction of phosphinic and phosphoric imidazolides 13 with sulfonic acid 6. c) Reaction of 13 with sulfonic anhydride 15. All methods result in high yields. Some chemical properties of the anhydrides 3 are described. Abstractde Phosphorsäure- und Phosphinsäure-sulfonsäure-anhydride – Neuuntersuchung und Korrekturen. Neue Synthese-Methoden Frühere Ergebnisse aus unseren und anderen Laboratorien an Phosphorsäure- und Phosphinsäure-sulfonsäure-anhydriden wurden überprüft. Es wurde jetzt gefunden, daß sich keine einzige früher beschriebene Reaktion als allgemeine Methode zur Darstellung gemischter Anhydride RR′P(O)SO2R″ mit hohen Ausbeuten an isolierten Produkten eignet. Die folgenden drei Verfahren zur Synthese von reinen Anhydriden 3 werden beschrieben: a) Die Trifluormethansulfonsäure-katalysierte Reaktion von Phosphinsäure 9 mit Sulfonsäure-triazoliden 10. b) Reaktion von Phosphinsäure- und Phosphorsäure-imidazoliden 13 mit der Sulfonsäure 6. c) Umsetzung von 13 mit Sulfonsäureanhydrid 15. Alle Methoden ergeben hohe Ausbeuten. Einige chemische Eigenschaften der Anhydride 3 werden beschrieben. Citing Literature Volume115, Issue4April 1982Pages 1636-1643 RelatedInformation