Methylene blue cation → HCID 86591448, compound

Participants

Reaction Steps

A solution of 3-(4′-bromo-[1,1′-biphenyl]-4-yl)-2-butenol (4f, 500 mg) and methylene blue (5 mg) in CH3CN (35 ml) and CH2Cl2 (35 ml) was photooxygenated at −6° C. for 3.5 h. Cyclohexanone (1 ml) and p-toluenesulfonic acid (60 mg) were added and reaction mixture was left at r.t. for 18 h. The reaction mixture was diluted with saturated NaHCO3 solution (5 ml) and worked up as above and concentrated. Crude product was purified by column chromatography to furnish 320 mg (47% yield, based on allylic alcohol 4f, used) of trioxane 7fc, m.p. 118-120° C.

Provenance & Evidence