Azobisisobutyronitrile → Adamantane

Participants

Reaction Steps

A solution of 1-bromoadamantane (108 mg, 0.5 mmol, 1.0 equiv), the phosphonium supported chlorostanne (15) (82 mg, 0.1 mmol, 0.2 equiv), NaBH4 (28 mg, 0.75 mmol, 1.5 equiv) in CH3CN (2.5 mL, 0.2 M) was heated to reflux under Ar for 10 min. Then AIBN (8 mg, 0.05 mmol, 0.1 equiv) was added and the solution was heated to reflux for an additional 2 h. CHCl3 (5 mL) was added and the solution was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude product was diluted with CHCl3(1 ml) and the tin residues were precipitated by adding Et2O (10 mL). The mixture was filtered through Celite and the filtrate was evaporated to afford pure adamantane in quantitative yield. No traces (<1%) of stannane impurities could be detected by NMR.

Provenance & Evidence