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2‐furyloxirane: II. Reduction, hydrolysis, alcoholsis and the uncatalysed polymerization induced by OH groups
Author(s) -
Hilmi Amri,
Belgacem Mohamed Naceur,
Signoret Christian,
Gandini Alessandro
Publication year - 1996
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/(sici)1097-0126(199612)41:4<427::aid-pi633>3.0.co;2-b
Subject(s) - alkoxide , steric effects , polymerization , hydrolysis , chemistry , ring opening polymerization , polymer chemistry , catalysis , ring (chemistry) , lewis acids and bases , organic chemistry , polymer
The reduction of furyloxirane (FO) with different reducing agents was conducted under various experimental conditions and occurred essentially by the α‐opening of the oxirane ring. It was also shown that the presence of Lewis acids favoured this mode of ring opening. The hydrolysis of furanic oxiranes was accompanied by oligomerization even in the absence of a catalyst. Moreover, very small quantities of water induced the oligomerization of FO giving degrees of polymerization of 40–50. This behaviour is unique since aliphatic and aromatic oxiranes are not activated by water alone. The alcoholysis of FO catalysed by metal alkoxides showed variable extents of α‐ and β‐opening of the oxirane ring, depending on the steric hindrance of the alkoxide used.