Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes

R Alan Aitken*, Khadija Ait Moulay, David Bradford Cordes, Ryan Inwood, Fraser G. Jamieson, Alexander J. B. Nelson, Aidan McKay

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Downloads (Pure)

Abstract

A series of fourteen O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the ortho position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo cyclisation in eight cases to give the novel 2,3-dihydrobenzo[d][1,3]oxaphospholes in moderate to low yield as a single diastereomer for which the relative configuration has been determined by X-ray diffraction in one case.
Original languageEnglish
Pages (from-to)12-31
Number of pages20
JournalOrganics
Volume5
Issue number1
DOIs
Publication statusPublished - 1 Feb 2024

Keywords

  • 1,3-dihydrobenzo[d][1,3]oxaphosphole
  • 1,3-benzoxaphosphole
  • Phosphonamidate
  • X-ray structure
  • Hydrogen bonding

Fingerprint

Dive into the research topics of 'Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes'. Together they form a unique fingerprint.

Cite this