A truly multifunctional heterocycle: Iminophosphorane, N,P chelate, and dihydropyridine

D.A. Smith (1) , A.S. Batsanov , Karinne Miqueu (2) , Jean-Marc Sotiropoulos (3) , D.C. Apperley (4) , J.A.K. Howard (5) , P.W. Dyer (4)

1 CENBG - Centre d'Etudes Nucléaires de Bordeaux Gradignan
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
3 IPREM - Institut pluridisciplinaire de recherche sur l'environnement et les matériaux
4 DEPARTMENT OF CHEMISTRY
5 Chemistry Department

(Chemical Equation Presented) Three in one: The anellated σ4-1λ5-[1,3,2]diazaphosphole 2 exists in tautomeric equilibrium with isomer 1 (see scheme) and undergoes three completely different types of reaction: trimethyl aluminum binds at the N terminus of the P=N bond with ring retention, the dihydropyridine fragment reacts with an activated acetylene in a pseudo-[2+2] cycloaddition, and P-N bond cleavage is possible with RhI. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Domaines: Catalyse; Chimie de coordination; Chimie organique; Polymères; Chimie théorique et/ou physique

D.A. Smith, A.S. Batsanov, Karinne Miqueu, Jean-Marc Sotiropoulos, D.C. Apperley, et al.. A truly multifunctional heterocycle: Iminophosphorane, N,P chelate, and dihydropyridine. Angewandte Chemie International Edition, 2008, 47 (45), pp.8674-8677. ⟨10.1002/anie.200803373⟩. ⟨hal-01613259⟩