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Access to Bicyclo[4.2.0]octene Monomers To Explore the Scope of Alternating Ring-Opening Metathesis Polymerization.

ABSTRACT: Bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides undergo alternating ring-opening metathesis polymerization (AROMP) with cyclohexene. Herein, a general method for the preparation of bicyclo[4.2.0]oct-(8)-ene-8-carboxy derivatives is described. The central 8-cyano intermediate provides entry to five different functional group substituents on the alkene. These monomers were tested as potential substrates for AROMP with cyclohexene. In addition to the carboxamide, the carboxynitrile and carboxaldehyde are also substrates for AROMP. In the case of the carboxaldehyde, the polymer is regioregular. However, the addition of carboxynitrile is stereoirregular and slow.

SUBMITTER: Chen L

PROVIDER: S-EPMC5838619 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Access to Bicyclo[4.2.0]octene Monomers To Explore the Scope of Alternating Ring-Opening Metathesis Polymerization.

Chen Lei L Li Liqiang L Sampson Nicole S NS

The Journal of organic chemistry 20180214 5

Bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides undergo alternating ring-opening metathesis polymerization (AROMP) with cyclohexene. Herein, a general method for the preparation of bicyclo[4.2.0]oct-(8)-ene-8-carboxy derivatives is described. The central 8-cyano intermediate provides entry to five different functional group substituents on the alkene. These monomers were tested as potential substrates for AROMP with cyclohexene. In addition to the carboxamide, the carboxynitrile and carboxaldehyde are ...[more]

PMID: 29406722

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