Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid

Dominique C. Stepinski, Derek W. Nelson, Peter R. Zalupski, Albert W. Herlinger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

The 1H-tetrazole catalyzed coupling of methylenebis(phosphonic dichloride), CH2(POCl2)2, with primary alkyl, cyclic secondary alkyl, aromatic, and silicon- and fluorine-containing alcohols selectively affords symmetric P,P′-dialkyl partial esters as well as homoleptic and mixed tetraesters. Two partial ester intermediates, methylenebis(2-ethylhexyl phosphonic chloride) and 2-ethylhexyl methylenebisphosphonic trichloride, were observed by 1H- and 31P NMR spectroscopy in the esterification of CH2(POCl2)2 with 2-ethyl-1-hexanol.

Original languageEnglish (US)
Pages (from-to)8637-8645
Number of pages9
JournalTetrahedron
Volume57
Issue number41
DOIs
StatePublished - Oct 8 2001

Keywords

  • Aggregation
  • Esterification
  • Phosphonic acids and derivatives
  • Tetrazoles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid'. Together they form a unique fingerprint.

Cite this