Comparative reactivity of exo- and endo-isomers in the ru-initiated ring-opening metathesis polymerization of doubly functionalized norbornenes with both cyano and ester groups

Yasushi Nishihara; Yoshiaki Inoue; Yuushou Nakayama; Takeshi Shiono; Kentaro Takagi

doi:10.1021/ma061781c

Comparative reactivity of exo- and endo-isomers in the ru-initiated ring-opening metathesis polymerization of doubly functionalized norbornenes with both cyano and ester groups

Yasushi Nishihara, Yoshiaki Inoue, Yuushou Nakayama, Takeshi Shiono, Kentaro Takagi

Research Institute for Interdisciplinary Science

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

49 Citations (Scopus)

Abstract

A comparative study was conducted on the exo- and endo-isomers in the Ru-initiated ring-opening metathesis polymerization (ROMP) of doubly functionalized norborenes with both cyano and ester groups. Isometrically pure endo-form B and doubly functionalized exo-ethyl 3-cyanobicyclohept-5-ene-2- carboxylate (A)were prepared. The ROMP of exo-isomer A and endo-isomer B and the parent norborene were studied using the second-generation Grubbs' catalyst. The IR spectra of all the polymers obtained were very similar, while signals characteristics of the cyano group and ester carbonyl group at 2304 and 1734 cm^-1, respectively, were prominent features of the spectra. Compared to the parent norborene, cyano and ester functional groups seem to have an interaction with the Ru center, suppressing the polymerization.

Original language	English
Pages (from-to)	7458-7460
Number of pages	3
Journal	Macromolecules
Volume	39
Issue number	22
DOIs	https://doi.org/10.1021/ma061781c
Publication status	Published - Oct 31 2006

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/ma061781c

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Comparative reactivity of exo- and endo-isomers in the ru-initiated ring-opening metathesis polymerization of doubly functionalized norbornenes with both cyano and ester groups. / Nishihara, Yasushi; Inoue, Yoshiaki; Nakayama, Yuushou et al.

In: Macromolecules, Vol. 39, No. 22, 31.10.2006, p. 7458-7460.

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

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abstract = "A comparative study was conducted on the exo- and endo-isomers in the Ru-initiated ring-opening metathesis polymerization (ROMP) of doubly functionalized norborenes with both cyano and ester groups. Isometrically pure endo-form B and doubly functionalized exo-ethyl 3-cyanobicyclohept-5-ene-2- carboxylate (A)were prepared. The ROMP of exo-isomer A and endo-isomer B and the parent norborene were studied using the second-generation Grubbs' catalyst. The IR spectra of all the polymers obtained were very similar, while signals characteristics of the cyano group and ester carbonyl group at 2304 and 1734 cm-1, respectively, were prominent features of the spectra. Compared to the parent norborene, cyano and ester functional groups seem to have an interaction with the Ru center, suppressing the polymerization.",

author = "Yasushi Nishihara and Yoshiaki Inoue and Yuushou Nakayama and Takeshi Shiono and Kentaro Takagi",

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AU - Nishihara, Yasushi

AU - Inoue, Yoshiaki

AU - Nakayama, Yuushou

AU - Shiono, Takeshi

AU - Takagi, Kentaro

PY - 2006/10/31

Y1 - 2006/10/31

N2 - A comparative study was conducted on the exo- and endo-isomers in the Ru-initiated ring-opening metathesis polymerization (ROMP) of doubly functionalized norborenes with both cyano and ester groups. Isometrically pure endo-form B and doubly functionalized exo-ethyl 3-cyanobicyclohept-5-ene-2- carboxylate (A)were prepared. The ROMP of exo-isomer A and endo-isomer B and the parent norborene were studied using the second-generation Grubbs' catalyst. The IR spectra of all the polymers obtained were very similar, while signals characteristics of the cyano group and ester carbonyl group at 2304 and 1734 cm-1, respectively, were prominent features of the spectra. Compared to the parent norborene, cyano and ester functional groups seem to have an interaction with the Ru center, suppressing the polymerization.

AB - A comparative study was conducted on the exo- and endo-isomers in the Ru-initiated ring-opening metathesis polymerization (ROMP) of doubly functionalized norborenes with both cyano and ester groups. Isometrically pure endo-form B and doubly functionalized exo-ethyl 3-cyanobicyclohept-5-ene-2- carboxylate (A)were prepared. The ROMP of exo-isomer A and endo-isomer B and the parent norborene were studied using the second-generation Grubbs' catalyst. The IR spectra of all the polymers obtained were very similar, while signals characteristics of the cyano group and ester carbonyl group at 2304 and 1734 cm-1, respectively, were prominent features of the spectra. Compared to the parent norborene, cyano and ester functional groups seem to have an interaction with the Ru center, suppressing the polymerization.

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Comparative reactivity of exo- and endo-isomers in the ru-initiated ring-opening metathesis polymerization of doubly functionalized norbornenes with both cyano and ester groups

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