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09 mmol) at room temperature (ca. 20◦ ). The progress of the reaction was monitored by GLC, which indicated that acenaphthylene was converted into its 1,2-epoxide within one hour. Removal of the solvent on a rotary evaporator (20◦ , 15 mmHg) afforded a white solid, which was taken up into CH2 Cl2 (30 mL) and dried over Na2 SO4 . 77 (m, 6H). 5 h O (84%) O Bisbenzo[3 ,4 ]cyclobuta[1 ,2 :1,2:1 ,2 :3,4]biphenyleno[1,8b-b:2,3-b :4,4 a-b ]trisoxirene [Epoxidation of an Arene with DMD (in situ)]. 590 mmol).

2; EIMS m/z (%): 334 (M+ , 18). Anal. 38. 15. 9; EIMS m/z (%): 334 (M+ , 16). Anal. 38. 19. 80 mmol). The mixture was stirred at room temperature (ca. 20◦ ) for 30 minutes in the dark. The solvent was removed on a rotary evaporator (20◦ , 20 mmHg), to afford the title compound (62 mg, 84%). 80 mmol) at room temperature (ca. 20◦ ). After the reaction mixture was stirred for 12 hours, excess solvent was removed on a rotary evaporator (20◦ , 15 mmHg), and the residue was purified by preparative TLC on silica gel with CH2 Cl2 /hexane (1 : 1) as eluent.

The chemical nature of the ligand determines whether the oxidation takes place at a π bond (epoxidation), at a lone pair (heteroatom oxidation), or at a σ bond (Si–H insertion). Organometallic substrates with ligands that contain a reactive C=C double bond may undergo epoxidation. For example, the tungsten complex shown in Eq. ) to the corresponding α-hydroxy ketones after acidic workup (Eq. 212 If the metal complex is sufficiently robust, even electron-poor double bonds may be epoxidized under more strenuous conditions, as illustrated for the ferrocene derivative shown in Eq.

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