tert-Butyl hydroperoxide → (trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranemethanol

Participants

Reaction Steps

To a stirred solution of 103 mg (0.50 mmole) of (E)-9-phenyl-2-nonen-4,6,8-triyn-1-ol in 20 ml of dry benzene was added 5 mg of vanadyl acetylacetonate and 0.095 ml (0.50 mmole) of a 5.24M solution of t-butylhydroperoxide in benzene. Further 0.095 ml potions of t-butyl hydroperoxide solution were added after 2 hours and 31/2 hours. After stirring for 18 hours, the benzene solution was concentrated and purified via preparative thin layer chromatography (Analtech, 2 mm, silica gel; ether-hexane 1:1) to afford 59 mg of the title compound, melting point 68°-70° C.

Provenance & Evidence