Diphenyl phosphane chloride

Norboma-2,5-diene (0.95 mL, 9.4 mmol) and phenylacetylene (1.0 mL, 9.1 mmol) were added under to tris(acetylacetonato)cobalt (7.1 mg, 0.02 mmol) and (- -)-bicyclo[2.2.1]hept-5-ene-2,3-diylbis(diphenyl-phosphane) (14mg, 0.03 mmol) in dry THF (1 mL). The catalytically active cobalt species was then generated by adding 1 M diethylaluminum chloride in hexane (5 mL). The reaction mixture was stirred for 4h at 35 °C. i-PrOH (5mL) was added dropwise to decompose the excess of diethylaluminum chloride. The volatile constituents were removed by vacuum distillation at rt. The product was then isolated by vacuum distillation at lOO C in a Kugelrohr apparatus [a] 56.3 (c = 1, CHClj, 20°C). The H NMR and mass spectrum of the product were identical to those of a reference sample yield 100%, enantiomeric purity 98.4% ee, both determined by GC with naphthalene as standard using a 40-m Lipodex-C column. Retention times (—)-product 120.7 min, (-l-)-product 123.7 min (column temperature 104 C, carrier gas Hj, flow rate 4-5 mL min at 1.7 bar, injection temperature 170°C). 

---