Addition of secondary amines to alkynylphosphonates

✍ Scribed by Anna E. Panarina; Alla V. Dogadina; Valentin I. Zakharov; Boris I. Ionin

• Book ID: 104230777
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 73 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00711-0

✦ Synopsis

Addition of secondary amines to alkynylphosphonates catalyzed by Cu(I) salts proceeds regio-and stereospecifically to form (E)-2-(dialkylamino)alkenylphosphonates. The E-configuration was proved by analysis of 13 C-31 P vicinal spin-spin coupling constants in the NMR spectra of the products and authentic model compounds. The 3 J PC constants in the model compounds fall in the range of 6-12 Hz for the cis arrangement of the coupled nuclei and are equal to or higher than 16 Hz for the trans configuration. Related coupling constants in the addition products are around 5 Hz, that is, corresponding to cis coupling.