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A Phosphorus Analogue of Acenaphthylene
Author(s) -
Huang Haiyang,
Wei Zhibin,
Wang Mincan,
Duan Zheng,
Mathey François
Publication year - 2017
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.201700766
Subject(s) - chemistry , deprotonation , acenaphthylene , lone pair , molecule , double bond , methanol , crystallography , phosphorus , salt bridge , hydrogen bond , crystal structure , bond length , molecular geometry , stereochemistry , organic chemistry , ion , phenanthrene , biochemistry , mutant , gene
A 1‐phosphaacenaphthylene has been obtained by the deprotonation and collapse of the phosphorus bridge of an appropriate 7‐phosphanorbornenium salt. DFT computations showed that the molecule has an elongated P=C double bond of 1.736 Å with a strained C–P=C angle of 88.9°. The P lone pair corresponds to the HOMO–2. Its complexation by [W(CO) 5 ] or AuCl induced a clean addition of methanol and water to the P=C double bond. The water addition product was characterized by X‐ray crystal structure analysis.