Synthesis and Structures of Novel Pyridine-Bridged Phanes of 4,4′-Bipyridine

✍ Scribed by Holger Scheytza; Otto Rademacher; Hans-Ulrich Reißig

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 332 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199909)1999:9<2373::aid-ejoc2373>3.0.co;2-v

✦ Synopsis

Syntheses of nine novel phanes derived from 4,4Ј-bipyridine methyl)pyridine (1) to furnish compounds 16-18 in low yield.

Temperature-dependent NMR-spectroscopic studies of the incorporating new spacer elements are described together with their structural and spectroscopic properties. Starting macrocycles were performed to investigate their conformational behaviour. The X-ray crystal structures for from the previously unknown pyridine-bridged bis(4,4Јbipyridinium) dication 2 and various bis(bromomethyl)-phanes 3, 4 and 6 illustrate the preferred anti conformation of the macrocycles in the solid state. Consecutive reactions arenes, macrocycles 3-7 were prepared in a simple heterogeneous liquid-liquid reaction in satisfactory yields. In at the pyridine bridge were not successful; however, anisolophane 7 was converted into nitroanisolophane 11 by complementary experiments starting from bis(4,4Јbipyridinium) compounds 12-14 with substituted xylenes as simple nitration of the anisolo spacer in excellent yield. spacers, ring closure was performed with 2,6-bis(bromo-4,4Ј-bipyridine. We investigated structural pecularities and [a