Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Harry R. Hudson, Ádám Tajti, Erika Bálint, Mátyás Czugler, Konstantin Karaghiosoff, György Keglevich

Research output: Contribution to journalArticle

Abstract

A series of N-benzhydryl protected α-aminophosphonates with α-phenyl, α-(1-naphtyl), α-(9-anthryl) or α-(1-pyrenyl) substituents was synthesized by the Kabachnik–Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these α-aminophosphonates confirmed the presence of unusually short intramolecular Cα–Hδ+ ··· δ+H–Cperi contacts.

Original languageEnglish
Pages (from-to)1446-1455
Number of pages10
JournalSynthetic Communications
Volume50
Issue number10
DOIs
Publication statusPublished - May 18 2020

Keywords

  • C − H ··· H − C bonds
  • Kabachnik–Fields reaction
  • X-ray diffraction
  • crystal structure
  • microwave
  • α-Aminophosphonate

ASJC Scopus subject areas

  • Organic Chemistry

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