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Macrocycles, 5. Ring expansion of macrocyclic tin alkoxides with cyclic anhydrides

✍ Scribed by Hans R. Kricheldorf; Sven Eggerstedt

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 86 KB
Volume: 200
Category: Article
ISSN: 1022-1352
DOI: 10.1002/(sici)1521-3935(19990301)200:3<587::aid-macp587>3.0.co;2-d

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✦ Synopsis

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 Sn1O bonds. The resulting 30-and 17-membered macrocycles are stable up to temperatures around 115 8C 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(e-caprolactone) again no elimination of Bu 2 SnO was observed. After removal of the Bu 2 Sn groups under mild conditions telechelic poly(e-caprolactone)s with two carboxylic endgroups were isolated.

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