Oxygen → HCID 53937847, compound

Participants

Reaction Steps

The vinyl sulfide of Example 2(b) (0.100 g) was irradiated for 10 min in 20 mL of CH2Cl2 containing 2 mg of methylene blue with continuous oxygen bubbling at -40° C. using a 1000 W Na lamp. NCS (44.7 mg, 1 eq.) was added followed after 15 min by 100 mg (2.3 eq.) of 2,6-difluorophenol in 3 mL of CH2Cl2. The solution was allowed to warm to room temperature. After an hour, TLC showed a new material which emitted blue-green light when the plate was heated. The solution was evaporated, redissolved in a small amount of CH2Cl2 and the product isolated by two successive preparative TLC purifications first using 5-20% ethyl acetate in hexane and then using CH2Cl2 on a second plate yielding 11.2 mg of the product as a slightly yellow oil; 1H NMR (CDCl3) δ1.29-2.24 (m, 13H), 3.31 (br s, 1H), 5.00 (m, 1H), 6.68-7.6 (m, 7H).

Provenance & Evidence