Reaction #8657

Reaction equation

2-Methyladamantanyl methacrylate

methacrylonitrile

alpha-butyrolactone methacrylate

VAZO67

→

2-methyladamantanylmethacrylate methacrylonitrile alpha-butyrolactone Methacrylate

Solvents

—

hexanes

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherThe resulting colorless solution was deoxygenated
2. 2
   Otherby gently bubbling a stream of N2 through the stirring solution for 15 minutes
3. 3
   workup.ADDITIONwas then added to the refluxing mixture over 10 minutes
4. 4
   TemperatureThe polymerization was then refluxed
5. 5
   Temperaturecooled to room temperature
6. 6
   Filtrationfiltered
7. 7
   Otherdried
8. 8
   workup.DISSOLUTIONre-dissolved in 70 mL of tetrahydrofuran
9. 9
   Otherprecipitated into 800 mL of hexanes
10. 10
    Filtrationfiltered
11. 11
    Washwashed well with hexanes
12. 12
    Otherdried in a vacuum oven at 40° C. for 24 hours

Procedure

2-Methyladamantanyl methacrylate (14.21 g, 0.061 mol), methacrylonitrile (3.05 g, 0.045 mol), and alpha-butyrolactone methacrylate (7.74 g, 0.045 mol) were dissolved in 66 mL of tetrahydrofuran. The resulting colorless solution was deoxygenated by gently bubbling a stream of N2 through the stirring solution for 15 minutes, placed under N2, and heated to 90° C. (oil bath temperature). VAZO67 (0.58 g, 0.0030 mol) dissolved in 7 ml of tetrahydrofuran, was then added to the refluxing mixture over 10 minutes. The polymerization was then refluxed with stirring for 20 hours and cooled to room temperature. The polymer was isolated by precipitation into 800 mL of hexanes, filtered, dried, re-dissolved in 70 mL of tetrahydrofuran, precipitated into 800 mL of hexanes, filtered, washed well with hexanes, and dried in a vacuum oven at 40° C. for 24 hours. Yield 19.8 g (79% of theory). Composition of the title terpolymer was determined by quantitative C-13 NMR and was found to be within experimental error of the monomer feed ratio.

Source