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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 12
BKCSDE 29(12)
December 20, 2008 

Mechanism of Polymerization Reaction of 4-[(n-Butylsulfinyl)methyl]-4'-(chloromethyl)benzene
Sang Yong Pyun*, Whan Gi Kim, Jin Hyun Jeong, Bong Rae Cho*,
Elimination, Polymerization, Intermediate
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.
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