Synthesis of linear α-olefins via polyhomologation

Carl Wagner, Andrew A. Rodriguez, Kenneth J. Shea

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Linear α-olefins (LAOs) of controlled molecular weight and low PDI were synthesized in high yield by the polyhomologation reaction of dimethylsulfoxonium methylide (1) with triallylborane (2). Following polymerization, propionic acid or trimethylamine N-oxide dihydrate (TAO) was used to afford α-vinyl-ω-methyl or α-vinyl-ω-hydroxy end-functionalized polymethylene, respectively. Controllable molecular weights up to 13 kDa were obtained by varying the initial monomer/catalyst ratio, and the resultant polymers had very narrow polydispersities (PDI < 1.08). Although polymer yields were generally high, quantities of oxidized side products were observed in α-vinyl-ω-methyl samples; however, these oxidized side products could be removed for samples of low molecular weights (C n ≤ 36).

Original languageEnglish (US)
Pages (from-to)7286-7291
Number of pages6
JournalMacromolecules
Volume38
Issue number17
DOIs
StatePublished - Aug 23 2005
Externally publishedYes

Fingerprint

Alkenes
Olefins
Molecular weight
Polymers
Troleandomycin
Propionic acid
Polydispersity
Monomers
Polymerization
Catalysts
Oxides

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Synthesis of linear α-olefins via polyhomologation. / Wagner, Carl; Rodriguez, Andrew A.; Shea, Kenneth J.

In: Macromolecules, Vol. 38, No. 17, 23.08.2005, p. 7286-7291.

Research output: Contribution to journalArticle

Wagner, Carl ; Rodriguez, Andrew A. ; Shea, Kenneth J. / Synthesis of linear α-olefins via polyhomologation. In: Macromolecules. 2005 ; Vol. 38, No. 17. pp. 7286-7291.
@article{de3f0c7ee28b462192c9b8a7919b3a38,
title = "Synthesis of linear α-olefins via polyhomologation",
abstract = "Linear α-olefins (LAOs) of controlled molecular weight and low PDI were synthesized in high yield by the polyhomologation reaction of dimethylsulfoxonium methylide (1) with triallylborane (2). Following polymerization, propionic acid or trimethylamine N-oxide dihydrate (TAO) was used to afford α-vinyl-ω-methyl or α-vinyl-ω-hydroxy end-functionalized polymethylene, respectively. Controllable molecular weights up to 13 kDa were obtained by varying the initial monomer/catalyst ratio, and the resultant polymers had very narrow polydispersities (PDI < 1.08). Although polymer yields were generally high, quantities of oxidized side products were observed in α-vinyl-ω-methyl samples; however, these oxidized side products could be removed for samples of low molecular weights (C n ≤ 36).",
author = "Carl Wagner and Rodriguez, {Andrew A.} and Shea, {Kenneth J.}",
year = "2005",
month = "8",
day = "23",
doi = "10.1021/ma050152k",
language = "English (US)",
volume = "38",
pages = "7286--7291",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Synthesis of linear α-olefins via polyhomologation

AU - Wagner, Carl

AU - Rodriguez, Andrew A.

AU - Shea, Kenneth J.

PY - 2005/8/23

Y1 - 2005/8/23

N2 - Linear α-olefins (LAOs) of controlled molecular weight and low PDI were synthesized in high yield by the polyhomologation reaction of dimethylsulfoxonium methylide (1) with triallylborane (2). Following polymerization, propionic acid or trimethylamine N-oxide dihydrate (TAO) was used to afford α-vinyl-ω-methyl or α-vinyl-ω-hydroxy end-functionalized polymethylene, respectively. Controllable molecular weights up to 13 kDa were obtained by varying the initial monomer/catalyst ratio, and the resultant polymers had very narrow polydispersities (PDI < 1.08). Although polymer yields were generally high, quantities of oxidized side products were observed in α-vinyl-ω-methyl samples; however, these oxidized side products could be removed for samples of low molecular weights (C n ≤ 36).

AB - Linear α-olefins (LAOs) of controlled molecular weight and low PDI were synthesized in high yield by the polyhomologation reaction of dimethylsulfoxonium methylide (1) with triallylborane (2). Following polymerization, propionic acid or trimethylamine N-oxide dihydrate (TAO) was used to afford α-vinyl-ω-methyl or α-vinyl-ω-hydroxy end-functionalized polymethylene, respectively. Controllable molecular weights up to 13 kDa were obtained by varying the initial monomer/catalyst ratio, and the resultant polymers had very narrow polydispersities (PDI < 1.08). Although polymer yields were generally high, quantities of oxidized side products were observed in α-vinyl-ω-methyl samples; however, these oxidized side products could be removed for samples of low molecular weights (C n ≤ 36).

UR - http://www.scopus.com/inward/record.url?scp=24944591373&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=24944591373&partnerID=8YFLogxK

U2 - 10.1021/ma050152k

DO - 10.1021/ma050152k

M3 - Article

AN - SCOPUS:24944591373

VL - 38

SP - 7286

EP - 7291

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 17

ER -