Mechanism of polymerization reaction of 4-[(n-butylsulfinyl)methyl]-4′-(chloromethyl)benzene

Sang Yong Pyun, Whan Gi Kim, Jin Hyun Jeong, Bong Rae Cho

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The polymerization reaction of 4-[(n-butylsulfinyl)methyl]-4′-(chloromethyl)benzene (1a) with t-BuONa in CH2Cl2/monomethylformamide (MMF) (4/6) was studied kinetically. The reaction proceeds in two steps; the formation of a p-quinodimethane intermediate (M) followed by the polymerization of M. Results of kinetic studies and H-D exchange experiments reveal that the 1,6-elimination proceeds by the (E1cb)irr mechanism. The rate of the disappearance of M was increased by the carbanion and S2O82-, inhibited by TEMPO and unaltered by the addition of HCl. From these results, a free radical polymerization mechanism is proposed.

Original languageEnglish
Pages (from-to)2453-2458
Number of pages6
JournalBulletin of the Korean Chemical Society
Volume29
Issue number12
DOIs
Publication statusPublished - 2008 Dec

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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