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The effect of reaction conditions on the chain end structure and functionality during dehydrochlorination of tert ‐chlorinetelechelic polyisobutylene by potassium tert ‐butoxide
Author(s) -
Feldthusen Jesper,
Iván Béla,
Müller Axel H. E.
Publication year - 1998
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19981201)19:12<661::aid-marc661>3.0.co;2-a
Subject(s) - tetrahydrofuran , chlorine , chemistry , olefin fiber , polymer chemistry , potassium , telechelic polymer , chlorine atom , end group , organic chemistry , medicinal chemistry , polymerization , catalysis , polymer , solvent
Dehydrochlorination of tert ‐chlorine‐telechelic polyisobutylene with potassium tert ‐butoxide in refluxing tetrahydrofuran is quantitative after 22 h, but results in ca. 3% endo olefin chain ends which are not reactive in some subsequent functionalization reactions. The formation of these undesired structures is most likely due to simultaneous thermally induced HCl loss. Lower temperatures and longer reaction times led to exclusive formation of external double bonds in some cases but to incomplete dehydrochlorination.