A Phosphorus Analogue of Acenaphthylene. Issue 38 (7th August 2017)

• Record Type: Journal Article
• Authors: Huang, Haiyang; Wei, Zhibin; Wang, Mincan; Duan, Zheng; Mathey, François
• Is Part Of: European journal of organic chemistry. Issue 38(2017)
• Page Start: 5724
• Page End: 5728
• Publication Date: 2017-08-07
• Subjects: Phosphorus heterocycles -- Phosphaalkenes -- Density functional calculations -- Ylides -- X‐ray diffraction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700766
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The conversion of a λ 5 ‐P‐ylide into a λ 3 ‐phosphaalkene provides the first example of a 1‐phosphaacenaphthylene derivative.