Ethanepolyphosphonates: Convenient One-Pot Syntheses of Esters, Acids, and Salts with High Yields and Their Properties

Abstract

Polyfunctional phosphonates CHP*₂–CHP*₂, CH₂P*–CHP*₂, CHR′P*–CHP*₂ (P* = P(O)(OR)₂; R = Me, Et, iPr, iOct; R′ = Ph, Mes, CH₂P*) were synthesized from chlorinated ethylenes by reaction with sodium dialkyl phosphites (RO)₂PONa in THF using convenient one-pot procedures. Some corresponding acids (R = H) of general type H_nL and salts were described. Molecular structures were deduced from NMR and X-Ray studies. Noncanonical rotamers in overcrowded molecules are discussed.

GRAPHICAL ABSTRACT

Keywords:

• Polyphosphonates
• esters
• acids
• salts
• structures
• NMR

ACKNOWLEDGMENT

Particular thanks for dedicated work are due to members of the research team at Düsseldorf: M. Ackermann, W. Boenigk, U. Fischer, S. Goudetsidis, M. Grzonka, H. Papadopoulos, R. Peters, G. Piller, U. Prior, H. Spiegl, and E. Wilke.We were grateful for good external cooperations and wish to thank the following persons and institutions: X-Ray studies were performed by W. S. Sheldrick (Braunschweig-Stöckheim), D. Schomburg (Braunschweig-Stöckheim), and G. Becker (Stuttgart). Some 2D NMR studies were executed by M. Murray (Bristol) while help with 2D EXSY experiments came from K. Orrell and V. Sik (Exeter). Some chemicals were donated by Henkel KGaA (Düsseldorf) and Bayer AG (Leverkusen). Thanks are due to the Fonds der Chemischen Industrie e. V. for material support.Finally, the author would like to thank the referees for careful reading and suggestions.