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- W2004964488 abstract "It was shown in a previous paper that a number of m - and p-substituted β-nitrostyrenes would readily undergo polymerization via anionic initiation with alkoxide ions to yield high polymers, whereas, in all cases, the corresponding o-substituted isomers could not be induced to produce polymers under any conditions tried. This article reports a systematic study of this unexpected “ortho effect” based on the initial postulate that the effect was the result of steric inhibition of the propagation step that would ordinarily lead to polymer. Since the fluorine atom is only slightly larger than the hydrogen atom, the series o-, m-, and p-fluoro-β-nitrostyrenes was synthesized and its alkoxide ion-initiated polymerization studied. Although it was shown in all cases of o-substituted β-nitrostyrenes studied that initiation was rapid, only in the case of o-fluoro-β-nitrostyrene was a substantial amount of polymer obtained. With up to 3 mole % initiator a maximum of 26% polymer was obtained, whereas polymerization was rapid in cases of the meta and para isomers. The values of the propagation rate constants kp were found to be 1.1 liters/mole-sec for the para isomer as compared with 4.8 × 10−2 liter/mole-sec for the ortho isomer for a ratio kp(p)/kp(o) = 23, the magnitude of this ortho effect for the fluorine atom." @default.
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- W2004964488 date "1978-05-01" @default.
- W2004964488 modified "2023-09-23" @default.
- W2004964488 title "A pronounced ortho effect in the polymerization of o-substituted β-nitrostyrenes" @default.
- W2004964488 doi "https://doi.org/10.1002/pol.1978.170160508" @default.
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