Synthesis of polyenes from trichloromethyl derivatives

Klimov, V.I.; Raida, V. S.; Kryazhev, Yu. G.

doi:10.1016/0032-3950(79)90332-0

Cited by 2 publications

(2 citation statements)

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“…It was reasoned that the NMR signal suppression effects may be due to the presence of polymer‐based radicals in part because poly(phenyl carbyne)s have been previously reported to contain unpaired electrons 18–20 . Electron paramagnetic resonance (EPR) spectroscopy revealed that the polymers described above exhibited sharp signals at g = 2.002–2.003 with a separation of 8–10 G, consistent with carbon‐centered radicals.…”

Section: Resultsmentioning

confidence: 99%

“…Kryazhev et al reported (1969Kryazhev et al reported ( , 1979) that treatment of ⊍,⊍,⊍-trichlorotoluene (1) with an excess of lithium, magnesium or zinc leads to the formation of a linear, unsaturated polymer. 18,19 Bianconi and colleagues later found that exposing 1 to a sodium potassium amalgam afforded branched polymers that consisted primarily of sp 3 -hybridized carbons in the backbones. 20,21 Likewise, poly(carbyne)s derived from bromoform, chloroform and 1,1,1-trichloroethane have also been characterized as branched.…”

Section: Introductionmentioning

confidence: 99%

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Poly(carbyne)s via reductive C1 polymerization

Cahoon

Goossens

Bielawski

2020

Polymer International

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C1 polymerizations enable the synthesis of densely functionalized, persubstituted polymers that are challenging to access using conventional methods. One class of C1 polymers are the poly(carbyne)s, which are unique in that they can adopt branched or linear structures, or combinations thereof. Herein, we report the synthesis of new poly(carbyne)s, including those that feature side chains with carbonyl-containing functional groups. The polymers were obtained by exposing solutions of monomers outfitted with trihalomethyl or trimethyl orthoformate groups to metallic lithium, and reaction performance was improved when electron transfer agents (e.g. naphthalene) were included. The mechanisms of the polymerizations were also deconvoluted and found to depend on the monomer employed.

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Section: Resultsmentioning

confidence: 99%