Synthesis of 2‐Phosphaindolizine and [1,3]Azaphospholo[1,5‐ a ]quin­oline

Autor: Konstantin Karaghiosoff, Jörn Martens, Christina Hettstedt, Robert J. Mayer, Sarah Linert
Rok vydání: 2015
Předmět:
Zdroj: European Journal of Inorganic Chemistry. 2016:726-735
ISSN: 1099-0682
1434-1948
DOI: 10.1002/ejic.201501120
Popis: The reaction of (chloromethyl)dichlorophosphine (1) with 2-[(trimethylsilyl)methyl] pyridine (6) and 2-[(trimethylsilyl) methyl] quinoline (12) in THF affords unsubstituted parent 2-phosphaindolizine (5) and [1,3]azaphospholo[1,5-a] quinoline (7). Multinuclear low-temperature NMR spectroscopy was used to investigate the reaction mechanism;a cascade of substitution and cyclization steps involving transient picolylphosphines and phosphorus heterocycles was identified. The molecular and crystal structures of two heterocyclic intermediates and of 7 were determined by single-crystal X-ray diffraction. Moreover, all intermediates and products were characterized by multinuclear H-1, C-13 and P-31 NMR spectroscopy.
Databáze: OpenAIRE