Carbanionic Polymerization: General Aspects and Initiation

Fontanille, Michel

doi:10.1016/b978-0-08-096701-1.00087-2

Cited by 8 publications

(2 citation statements)

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“…Despite the potential for loss of functionality due to proton abstraction, this functionalization reaction was shown to be of synthetic value given that high functionality (higher than 90%) was found under the conditions used. Also, it was shown that the addition of a Lewis base produced a more reactive poly(styryl)lithium chain end, , which led to a faster rate of chain-end functionalization without any significant change of the extent of functionalization. The regiochemistry at the chain end was shown to be 97% the product of the expected attack of poly(styryl)lithium on the least hindered carbon of the propylene oxide ring and 3% the product of the least probable attack on the methine carbon of propylene oxide.…”

Section: Discussionmentioning

confidence: 99%

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Investigation of the Reaction of Poly(styryl)lithium with Propylene Oxide

Quirk

Lizarraga

1998

Macromolecules

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The room-temperature functionalization reaction between poly(styryl)lithium and propylene oxide in benzene was studied. The functionalized polymer was characterized by 1H NMR, 13C NMR, and APT-13C NMR. 13C-methyl-labeled propylene oxide-functionalized polystyrene was also synthesized and characterized. Hydroxylated polystyrene was obtained in only 93% yield, but with high regioselectivity (97% of addition of the anionic chain-end to the least substituted carbon of the propylene oxide ring) and no oligomerization. The lower than quantitative yield was ascribed to the proton-transfer reaction of poly(styryl)lithium from the methyl group of propylene oxide, which formed unfunctionalized polystyrene.

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Section: Discussionmentioning

confidence: 99%

“…Living anionic polymerization is a particularly suitable way to effect chain-end functionalization, given that it generates stable polymer chain ends, once all the monomer is consumed. Reactions of the living polymer chain end with a variety of electrophiles have been carried out to generate different functional groups. − …”

Section: Introductionmentioning

confidence: 99%