Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride

Bong Rae Cho; Tae Hoon Kim; Yong Kwan Kim; Nam Soo Kim

doi:10.1021/ma980483f

Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride

Bong Rae Cho, Tae Hoon Kim, Yong Kwan Kim, Nam Soo Kim

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

9 Citations (Scopus)

Abstract

The polymerization kinetics of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride were studied. The reaction proceeds via a 2,5-dihydrothiophene intermediate M. Results of kinetic and product studies revealed that the 1,6-elimination proceeded by an (E1cb)_irr mechanism. The rate of the disappearance of M was not influenced by the addition of OH^-, carbanions, and tetrahydrothiophene but was accelerated by S₂O₈^2- and inhibited by TEMPO. In addition, the reaction mixture exhibited an electron spin resonance signal with a g value of 2.003 G and induced the polymerization of acrylamide. These results indicated a free radical polymerization mechanism.

Original language	English
Pages (from-to)	3583-3589
Number of pages	7
Journal	Macromolecules
Volume	32
Issue number	11
DOIs	https://doi.org/10.1021/ma980483f
Publication status	Published - 1999 Jun 1

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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abstract = "The polymerization kinetics of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride were studied. The reaction proceeds via a 2,5-dihydrothiophene intermediate M. Results of kinetic and product studies revealed that the 1,6-elimination proceeded by an (E1cb)irr mechanism. The rate of the disappearance of M was not influenced by the addition of OH-, carbanions, and tetrahydrothiophene but was accelerated by S2O82- and inhibited by TEMPO. In addition, the reaction mixture exhibited an electron spin resonance signal with a g value of 2.003 G and induced the polymerization of acrylamide. These results indicated a free radical polymerization mechanism.",

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T1 - Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride

AU - Cho, Bong Rae

AU - Kim, Tae Hoon

AU - Kim, Yong Kwan

AU - Kim, Nam Soo

PY - 1999/6/1

Y1 - 1999/6/1

N2 - The polymerization kinetics of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride were studied. The reaction proceeds via a 2,5-dihydrothiophene intermediate M. Results of kinetic and product studies revealed that the 1,6-elimination proceeded by an (E1cb)irr mechanism. The rate of the disappearance of M was not influenced by the addition of OH-, carbanions, and tetrahydrothiophene but was accelerated by S2O82- and inhibited by TEMPO. In addition, the reaction mixture exhibited an electron spin resonance signal with a g value of 2.003 G and induced the polymerization of acrylamide. These results indicated a free radical polymerization mechanism.

AB - The polymerization kinetics of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride were studied. The reaction proceeds via a 2,5-dihydrothiophene intermediate M. Results of kinetic and product studies revealed that the 1,6-elimination proceeded by an (E1cb)irr mechanism. The rate of the disappearance of M was not influenced by the addition of OH-, carbanions, and tetrahydrothiophene but was accelerated by S2O82- and inhibited by TEMPO. In addition, the reaction mixture exhibited an electron spin resonance signal with a g value of 2.003 G and induced the polymerization of acrylamide. These results indicated a free radical polymerization mechanism.

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Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride

Abstract

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