反应详情

温度

190 °C

A mixture of 7-bromo-9,9-didecylfluorene-2carbaldehyde (example 2; 6.6 g, 12 mmol), dithiooxamide (rubeanic acid, 0.6 g, 5 mmol) and DMSO (4 mL) was heated in an oil-bath to a bath temperature of 190° C., held 1 hour and poured onto water. The mixture was extracted into toluene (200 mL). The toluene extract was washed with water, dried and concentrated. The resulting residue was chromatographed over alumina to get a mixture of product containing the aldehyde product. The mixture was rechromatographed over silica gel, and elution with toluene gave 0.9 g (15% yield) of the product which was recrystallized from a mixture of heptane and hexanes to get pure product 0.6 g, (10% yield), m.p. 150.8-152.7° C. Mass Spec.(m/z): 1186, 1188, 1190 (M+). Anal. Calcd. for C70H96Br2N2S2: C, 70.68%; H, 8.14%; N, 2.36%; S, 5.39%; Br, 13.44%. Found: C, 70.69%; H, 8.22%; N, 2.07%; S, 5.31%; Br, 13.67%.

1. additionpoured onto water
2. extractionThe mixture was extracted into toluene (200 mL)
3. extractionThe toluene extract
4. washwas washed with water
5. customdried
6. concentrationconcentrated
7. customThe resulting residue was chromatographed over alumina
8. customto get
9. additiona mixture of product
10. customThe mixture was rechromatographed over silica gel, and elution with toluene