Synthesis of Phenylalaninol Polymer (12)

 A schlenk flask was placed under vacuum for 24 hours at 50 C containing 0.91

grams phenylalaninol diene monomer (6) and a small stir bar. After 24 hours, 6.5 mg

(7.66 x 10 -3 mmol) of 2nd generation Grubbs' catalyst was added to the schlenk flask and

diluted with 0.5 mL of dry THF. The mixture was stirred under an argon atmosphere at

50 C for five days. Dry THF was added in 2-3 mL aliquots periodically to maintain low

viscosity. After polymerization was determined to be complete, a small volume of THF

was added to dissolve the polymer (12). The resultant polymer solution was placed on a

Teflon film-casting dish and the solvent was allowed to evaporate. H NMR (300 MHz,

CDC13, ppm): 6 1.18-1.41 (m, 18H), 1.44-1.71 (m, 4H), 1.91-2.05 (m, 4H), 2.07-2.14 (t,

2H), 2.26-2.36 (t, 2H), 2.72-2.92 (m, 2H), 3.99-4.12 (m, 2H), 4.38-4.5 (m, 1H), 4.89-5.03

(m, 4H), 5.31-5.39 (m, 2H), 5.62-5.74 (s, 1H), 7.18-7.36 (m, 6H). 13C NMR (75 MHz,

CDC13, ppm): 6 25.18, 25.90, 29.22, 29.41, 29.58, 29.70, 29.85, 32.82, 34.41, 37.06,

37.77, 49.59, 64.83, 126.96, 128.82, 129.45, 172.99, 174.12.

Hydrogenation of Olefins

Hydrogenation of Glycinol Polymer (13)

 A (0.491 g) film of the glycinol olefin (13) was dissolved in toluene (40 mL). 25

mg of Wilkinson's catalyst was added to the solution. The solution was placed in a Parr

Bomb hydrogenation chamber. The solution was stirred under 800 psi H2 at 80 C for

four days. The resulting solution was filtered through a small plug of Celite in order to

remove the Wilkinson's catalyst. This solution was precipitated into ice-cold methanol in

a 100:1 volume ratio of methanol to CHC13. The insoluble high molecular weight

polymer was then filtered on a Kontes filtration apparatus using a 0.45 micron Teflon

filter. The collected polymer (13) was dissolved in CHC13 and cast on a Teflon film-