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Synthesis of 2‐Phosphaindolizine and [1,3]Azaphospholo[1,5‐ a ]quinoline
Author(s) -
Hettstedt Christina,
Mayer Robert J.,
Martens Jörn F.,
Linert Sarah,
Karaghiosoff Konstantin
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201501120
Subject(s) - chemistry , quinoline , trimethylsilyl , pyridine , nuclear magnetic resonance spectroscopy , single crystal , crystal structure , spectroscopy , medicinal chemistry , stereochemistry , crystallography , organic chemistry , physics , quantum mechanics
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 1 H, 13 C and 31 P NMR spectroscopy.