Synthesis and characterization of the very bulky phenols Ar*OH and Ar′OH (Ar* = C6H3-2,6-Trip2, Trip = C6H2-2,4,6-iPr3; Ar′ = C6H3-2,6-Dipp2, Dipp = C6H3-2,6-iPr2) and their lithium and sodium derivatives (LiOAr′)2 and (NaOAr*)2

The very bulky phenols (ArOH)-O-* (1) and Ar'OH (2), where Ar-* = C6H3-2,6-Trip(2) (Trip = C6H2-2,4,6-iPr(3)) and Ar' = C6H3- 2,6-Dipp(2) (Dipp = C6H3-2,6-iPr(2)), as well as their lithium and sodium derivatives (LiOAr*)(2) (3), (LiOAr')(2) (4) and (NaOAr*)(2) (5) have been synthesized and characterized. The terphenols 1 and 2 were obtained by the reaction of the aryllithium reagents with nitrobenzene and were isolated in ca. 70% yield. The lithium or sodium salts 3-5 were isolated by the reaction of 1 or 2 with nBuLi or sodium metal. All compounds were characterized spectroscopically, and by X-ray crystallography in the case of 1, 2, 4 and 5. The large terphenyl substituents prevent hydrogen-bonded association of the phenols 1 and 2. Instead, the O-H hydrogens interact with the pi-electron cloud on one of the flanking Trip or Dipp rings. The dimeric structures of 4 and 5 are relatively rare examples of structurally characterized alkali metal phenoxides that are unsolvated by internal electron pair donors or classical Lewis bases such as ethers or amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).