Synthesis of 5,5'-bi-2-oxaadamantane

Abstract

Although the synthesis and chemistry of heteroadamantanes have received considerable attention,1 3,3'bi(2,4,10-trioxaadamantane) (2) is the only known 1,1'-

Synthesis of rigid cores based on 1,1′-biadamantane

“…16 With a catalytic amount of AlCl 3 , 2b was also afforded by treatment of 1 with bromine for 3 h at room temperature in 89% yield. 17 Further functionalization of the bridgehead positions in 1,1 0biadamantyl scaffold, generally speaking, becomes more difficult with increasing substituents attached to the other bridgehead positions. 18,19 Inspired by the pioneering works of Teager 17 and Reinhardt, 16 we envisioned that by proper choices of Lewis acid catalysts and severity of conditions, six bromines can be introduced, all at the available bridgehead positions.…”

“…17 Further functionalization of the bridgehead positions in 1,1 0biadamantyl scaffold, generally speaking, becomes more difficult with increasing substituents attached to the other bridgehead positions. 18,19 Inspired by the pioneering works of Teager 17 and Reinhardt, 16 we envisioned that by proper choices of Lewis acid catalysts and severity of conditions, six bromines can be introduced, all at the available bridgehead positions. On this ground, the bromination was conducted by treating 1 with Br 2 in the presence of AlCl 3 at 85 C for 48 h to afford 2c in 70% yield.…”