Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization

Li Tan; Guofang Li; Kathlyn A. Parker; Nicole S. Sampson

doi:10.1021/acs.macromol.5b01058

Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization

Li Tan
, Guofang Li
, Kathlyn A. Parker
, Nicole S. Sampson

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

We describe an isomerization-alternating ROMP protocol that gives linear copolymers with rigorous sequence alternation. Bicyclo[4.2.0]oct-7-ene-7-carboxamides of primary amines are isomerized in the presence of (3-BrPyr)₂Cl₂(H₂IMes)Ru=CHPh to the corresponding bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides in which the olefinic bond is tetrasubstituted. The isomerized amides undergo alternating ring-opening metathesis polymerization with cyclohexene to provide soluble and linear copolymers with molecular weights up to ∼130 kDa. This process provides efficient entry to strictly alternating copolymers that can display diverse functional groups.

Original language	English
Pages (from-to)	4793-4800
Number of pages	8
Journal	Macromolecules
Volume	48
Issue number	14
DOIs	https://doi.org/10.1021/acs.macromol.5b01058
State	Published - Jul 28 2015

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title = "Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization",

abstract = "We describe an isomerization-alternating ROMP protocol that gives linear copolymers with rigorous sequence alternation. Bicyclo[4.2.0]oct-7-ene-7-carboxamides of primary amines are isomerized in the presence of (3-BrPyr)2Cl2(H2IMes)Ru=CHPh to the corresponding bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides in which the olefinic bond is tetrasubstituted. The isomerized amides undergo alternating ring-opening metathesis polymerization with cyclohexene to provide soluble and linear copolymers with molecular weights up to ∼130 kDa. This process provides efficient entry to strictly alternating copolymers that can display diverse functional groups.",

author = "Li Tan and Guofang Li and Parker, \{Kathlyn A.\} and Sampson, \{Nicole S.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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doi = "10.1021/acs.macromol.5b01058",

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T1 - Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization

AU - Tan, Li

AU - Li, Guofang

AU - Parker, Kathlyn A.

AU - Sampson, Nicole S.

PY - 2015/7/28

Y1 - 2015/7/28

N2 - We describe an isomerization-alternating ROMP protocol that gives linear copolymers with rigorous sequence alternation. Bicyclo[4.2.0]oct-7-ene-7-carboxamides of primary amines are isomerized in the presence of (3-BrPyr)2Cl2(H2IMes)Ru=CHPh to the corresponding bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides in which the olefinic bond is tetrasubstituted. The isomerized amides undergo alternating ring-opening metathesis polymerization with cyclohexene to provide soluble and linear copolymers with molecular weights up to ∼130 kDa. This process provides efficient entry to strictly alternating copolymers that can display diverse functional groups.

AB - We describe an isomerization-alternating ROMP protocol that gives linear copolymers with rigorous sequence alternation. Bicyclo[4.2.0]oct-7-ene-7-carboxamides of primary amines are isomerized in the presence of (3-BrPyr)2Cl2(H2IMes)Ru=CHPh to the corresponding bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides in which the olefinic bond is tetrasubstituted. The isomerized amides undergo alternating ring-opening metathesis polymerization with cyclohexene to provide soluble and linear copolymers with molecular weights up to ∼130 kDa. This process provides efficient entry to strictly alternating copolymers that can display diverse functional groups.

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DO - 10.1021/acs.macromol.5b01058

M3 - Article

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SN - 0024-9297

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JO - Macromolecules

JF - Macromolecules

IS - 14

ER -

Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization

Abstract

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