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Macrocycles, 5. Ring expansion of macrocyclic tin alkoxides with cyclic anhydrides
Author(s) -
Kricheldorf Hans R.,
Eggerstedt Sven
Publication year - 1999
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19990301)200:3<587::aid-macp587>3.0.co;2-d
Subject(s) - succinic anhydride , chemistry , tin , polymer chemistry , monomer , glutaric acid , succinic acid , dioxolane , ring (chemistry) , organic chemistry , polymer
At moderate temperatures the dimeric 2,2‐dibutyl‐2‐stanna‐1,3‐dioxolane (DSDOL) and the monomeric 2,2‐dibutyl‐2‐stanna‐1,3‐dioxepane (DSDOP) add to equivalents of succinic anhydride by a clean insertion reaction into the Sn—O bonds. The resulting 30‐ and 17‐membered macrocycles are stable up to temperatures around 115°C and do not eliminate Bu 2 SnO in the contrast to literature reports. When succinic or glutaric acid were added to tin‐containing macrocyclic poly( ε ‐caprolactone) again no elimination of Bu 2 SnO was observed. After removal of the Bu 2 Sn groups under mild conditions telechelic poly( ε ‐caprolactone)s with two carboxylic endgroups were isolated.