1,8-Bis(phosphino)naphthalenes: Synthesis and molecular structures

✍ Scribed by Atilla Karaçar; Holger Thönnessen; Peter G. Jones; Rainer Bartsch; Reinhard Schmutzler

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 291 KB
• Volume: 8
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1997)8:6<539::aid-hc14>3.0.co;2-s

✦ Synopsis

A series of 1,8-bis(phosphino)naphthalenes 2 was prepared by treating 1,8-dilithionaphthalene with the appropriate chloro-or bromophosphines RRЈPX; R, RЈ ‫ס‬ Me (for 2a), iPr (for 2c), Cy (for 2d), Ph (for 2f); R ‫ס‬ tBu, RЈ ‫ס‬ Ph (for 2e) (X ‫ס‬ Cl) and R, RЈ ‫ס‬ Et; X ‫ס‬ Br (for 2b). The resulting bisphosphines were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. X-ray crystal structure analyses were performed for 1,8-bis(diisopropylphosphino)naphthalene (2c), 1,8-bis(dicyclohexylphosphino)naphthalene (2d), and rac-1,8-bis(tert-butylphenylphosphino)naphthalene (2c). In each case, the proximity of the PR 2 groups leads to distortion,the main feature of which is the out-of-plane displacement of the P atoms. However, the distortions arising from the bulky PCy 2 groups in 2d were remarkably small.