POLYMERIZATION OF ALPHA-N-ALKYLSTYRENES .I. PREPARATION OF ALPHA-N-ALKYLSTYRENES

The Wittig reaction was used to prepare a series of new, pure, isomer-free α-n-alkylstyrenes. α-Pentyl-, α-heptyl-, α-nonyl-, α-undecyl-, α-tridecyl-, α-pentadecyl-, and α-heptadecylstyrene were prepared in 50-68% yields. To date, no pure, isomer-free α-n-alkylstyrene (alkyl > C2H5) has been reported. The identity of the new compounds was established by infrared spectroscopy and elemental analysis, and their homogeneity-was proven by gas-liquid partition chromatography. As a preliminary experiment, the homopolymerization behavior of α-heptylstyrene and α-nonylstyrene were studied using sodium naphthalene as the catalyst at -15°. Both compounds formed low molecular weight polymers after 72 hr. The experimental evidence indicates that if an α-n-alkylstyrene is devoid of isomers, steric hindrance will not prevent homopolymerization. © 1969, American Chemical Society. All rights reserved.