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Cationic polymerization behavior of seven-membered cyclic sulfite

✍ Scribed by Natsuhiro Azuma; Fumio Sanda; Toshikazu Takata; Takeshi Endo

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 237 KB
Volume: 35
Category: Article
ISSN: 0887-624X
DOI: 10.1002/(sici)1099-0518(199712)35:17<3673::aid-pola6>3.0.co;2-t

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✦ Synopsis

Cationic ring-opening polymerization behavior of a seven-membered cyclic sulfite ( 1) was examined. 1 was prepared by the reaction of 1,4-butanediol with SOCl 2 in 58% yield. The cationic polymerization of 1 was carried out at 0, 25, 60, or 100ЊC with trifluoromethanesulfonic acid (TfOH), methyl trifluoromethanesulfonate (TfOMe), BF 3 rOEt 2 , SnCl 4 , methyl p-toluenesulfonate (TsOMe), or MeI as an initiator in bulk under a nitrogen atmosphere to afford the polymer with M V n 1000-10,400. The order of activities of the initiators for 1 was as follows, TfOH à TfOMe ú SnCl 4 ú BF 3 rOEt 2 ú TsOMe à MeI. The polymerization of 1 with TfOMe afforded a poly(sulfite) below 25ЊC, but afforded a polymer containing an ether unit at 60ЊC, which was formed by a desulfoxylation. The higher the activity of the initiator was, the more easily the desulfoxylation occurred. We expected volume expansion on polymerization because cyclic sulfites have large dipole moment values, but it turned out that 1 showed 4.34% shrinkage on polymerization.

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