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 language | English |
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Pages (from-to) | 2453-2458 |
Number of pages | 6 |
Journal | Bulletin of the Korean Chemical Society |
Volume | 29 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2008 Dec |
Keywords
- Elimination
- Intermediate
- Polymerization
ASJC Scopus subject areas
- Chemistry(all)