Alternating copolymers of functional alkenes with carbon monoxide

Smita Kacker; Zhaozhong Jiang; Ayusman Sen

doi:10.1021/ma960255q

Alternating copolymers of functional alkenes with carbon monoxide

Smita Kacker, Zhaozhong Jiang, Ayusman Sen

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68 Scopus citations

Abstract

The alternating copolymerization of functional alkenes, CH₂=CH(CH₂)_xOH (x = 2, 3, 4, 9), CH₂=CH(CH₂)_xCOOH (x = 1, 2, 4, 8), and 4-allylanisole, with carbon monoxide was achieved by using [Pd(Me-DUPHOS)(MeCN)₂](BF₄)₂ [Me-DUPHOS = 1,2-bis(2,5-dimethylphospholano)benzene] as the catalyst. The resultant polymers were optically active with isotactic sequences in the backbone. With most alkenes, the polymers had poly(1,4-ketone) and/or "regular" poly(spiroketal) (i.e., 1,6-dioxaspiro-[4.4]nonane) enchainments. However, with 4-penten-1-ol and 3-buten-1-ol, the participation of the pendant hydroxyl group in intrachain reactions led to the formation of unusual polycyclic repeating units in the backbone. A comparison of [Pd(Me-DUPHOS)(MeCN)₂](BF₄)₂ with [Pd(DPPP)(MeCN)₂](BF₄)₂ [DPPP = 1,3-bis(diphenylphosphino)propane] indicated that the former was a significantly better catalyst for the alternating copolymerization of alkenols and alkenoic acids with carbon monoxide.

Original language	English (US)
Pages (from-to)	5852-5858
Number of pages	7
Journal	Macromolecules
Volume	29
Issue number	18
DOIs	https://doi.org/10.1021/ma960255q
State	Published - Aug 26 1996

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Alternating copolymers of functional alkenes with carbon monoxide",

abstract = "The alternating copolymerization of functional alkenes, CH2=CH(CH2)xOH (x = 2, 3, 4, 9), CH2=CH(CH2)xCOOH (x = 1, 2, 4, 8), and 4-allylanisole, with carbon monoxide was achieved by using [Pd(Me-DUPHOS)(MeCN)2](BF4)2 [Me-DUPHOS = 1,2-bis(2,5-dimethylphospholano)benzene] as the catalyst. The resultant polymers were optically active with isotactic sequences in the backbone. With most alkenes, the polymers had poly(1,4-ketone) and/or {"}regular{"} poly(spiroketal) (i.e., 1,6-dioxaspiro-[4.4]nonane) enchainments. However, with 4-penten-1-ol and 3-buten-1-ol, the participation of the pendant hydroxyl group in intrachain reactions led to the formation of unusual polycyclic repeating units in the backbone. A comparison of [Pd(Me-DUPHOS)(MeCN)2](BF4)2 with [Pd(DPPP)(MeCN)2](BF4)2 [DPPP = 1,3-bis(diphenylphosphino)propane] indicated that the former was a significantly better catalyst for the alternating copolymerization of alkenols and alkenoic acids with carbon monoxide.",

author = "Smita Kacker and Zhaozhong Jiang and Ayusman Sen",

year = "1996",

month = aug,

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doi = "10.1021/ma960255q",

language = "English (US)",

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pages = "5852--5858",

journal = "Macromolecules",

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publisher = "American Chemical Society",

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T1 - Alternating copolymers of functional alkenes with carbon monoxide

AU - Kacker, Smita

AU - Jiang, Zhaozhong

AU - Sen, Ayusman

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N2 - The alternating copolymerization of functional alkenes, CH2=CH(CH2)xOH (x = 2, 3, 4, 9), CH2=CH(CH2)xCOOH (x = 1, 2, 4, 8), and 4-allylanisole, with carbon monoxide was achieved by using [Pd(Me-DUPHOS)(MeCN)2](BF4)2 [Me-DUPHOS = 1,2-bis(2,5-dimethylphospholano)benzene] as the catalyst. The resultant polymers were optically active with isotactic sequences in the backbone. With most alkenes, the polymers had poly(1,4-ketone) and/or "regular" poly(spiroketal) (i.e., 1,6-dioxaspiro-[4.4]nonane) enchainments. However, with 4-penten-1-ol and 3-buten-1-ol, the participation of the pendant hydroxyl group in intrachain reactions led to the formation of unusual polycyclic repeating units in the backbone. A comparison of [Pd(Me-DUPHOS)(MeCN)2](BF4)2 with [Pd(DPPP)(MeCN)2](BF4)2 [DPPP = 1,3-bis(diphenylphosphino)propane] indicated that the former was a significantly better catalyst for the alternating copolymerization of alkenols and alkenoic acids with carbon monoxide.

AB - The alternating copolymerization of functional alkenes, CH2=CH(CH2)xOH (x = 2, 3, 4, 9), CH2=CH(CH2)xCOOH (x = 1, 2, 4, 8), and 4-allylanisole, with carbon monoxide was achieved by using [Pd(Me-DUPHOS)(MeCN)2](BF4)2 [Me-DUPHOS = 1,2-bis(2,5-dimethylphospholano)benzene] as the catalyst. The resultant polymers were optically active with isotactic sequences in the backbone. With most alkenes, the polymers had poly(1,4-ketone) and/or "regular" poly(spiroketal) (i.e., 1,6-dioxaspiro-[4.4]nonane) enchainments. However, with 4-penten-1-ol and 3-buten-1-ol, the participation of the pendant hydroxyl group in intrachain reactions led to the formation of unusual polycyclic repeating units in the backbone. A comparison of [Pd(Me-DUPHOS)(MeCN)2](BF4)2 with [Pd(DPPP)(MeCN)2](BF4)2 [DPPP = 1,3-bis(diphenylphosphino)propane] indicated that the former was a significantly better catalyst for the alternating copolymerization of alkenols and alkenoic acids with carbon monoxide.

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Alternating copolymers of functional alkenes with carbon monoxide

Abstract

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