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Stable N ‐Phosphanyl Acyclic Diaminocarbenes
Author(s) -
Marchenko Anatoliy,
Koidan Georgyi,
Hurieva Anastasiya,
Kurpiieva Olena,
Vlasenko Yurii,
Rozhenko Alexander B.,
Kostyuk Aleksandr
Publication year - 2014
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.201402166
Subject(s) - chemistry , deprotonation , carbene , aryl , nitrogen atom , carbon atom , nitrogen , carbon fibers , phosphorus , crystallography , stereochemistry , atom (system on chip) , substitution (logic) , medicinal chemistry , bond length , x ray crystallography , diffraction , crystal structure , catalysis , ring (chemistry) , organic chemistry , ion , alkyl , materials science , composite number , computer science , programming language , composite material , embedded system , physics , optics
The deprotonation of N ‐di‐ tert ‐butylphosphanyl‐ N ‐aryl‐ N′ ‐diisopropylformamidinium salts led to a new type of stable acyclic N ‐phosphanyl‐diaminocarbene (PADC). Carbenes 8a – 8d were separated as single compounds. The molecular structure of 8c was determined by X‐ray diffraction analysis. The PADC 8 possess an optimal substitution pattern at the nitrogen atoms, and the N–C carbene –N bond angle is 120.7°. Structural changes near the carbenic carbon atom, such as substitution of phenyl with mesityl, phosphanyl with selenophosphoryl, or the diisopropylamino group with 2,2,6,6‐tetramethylpiperidino, rendered them unstable. The PADCs underwent N,C‐phosphorus shifts to afford new C ‐phosphanylformamidines.