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On the Reactivity of Bisphosphirane‐Fused Anthracene towards Dichalcogenide Bonds, IPr Carbene, 2,6‐Diisopropylphenyl Isocyanide and Trimethylsilyl Azide
Author(s) -
Luo Qing,
Liu Tingting,
Huang Linlin,
Li Qianli,
Lu Wei
Publication year - 2025
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202500071
Subject(s) - isocyanide , chemistry , carbene , trimethylsilyl azide , anthracene , reactivity (psychology) , trimethylsilyl , azide , photochemistry , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract The development of phosphinidene precursors capable of releasing free phosphinidenes holds great potential in exploiting their reactivity with small molecules and enthalpically strong bonds. We report the facile cleavage of dichalcogenide bonds, including S−S, Se−Se and Te−Te bonded complexes over the phosphorus center of a bisphosphirane‐fused anthracene ( 1 ), which produces a variety of phosphonodichalcogenides ( 2 ‐ 4 ). We also show the ambiphilic nature of 1 . The reaction of 1 with nucleophiles, such as 1,3‐bis( iso propyl)imidazol‐2‐ylidene (I i Pr) and 2,6‐diisopropylphenyl isocyanide (DipNC) gives a phosphinidene adduct of I i Pr and a 1‐phospha‐3‐azaallene, respectively. Treatment of 1 with trimethylsilyl azide (TMSN 3 ) affords an iminophosphanide, manifesting the nucleophilic nature of 1 . These compounds were fully characterized by single‐crystal X‐ray diffraction (SC‐XRD) and spectroscopic analysis.

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