Synthesis of new cores and their use in the preparation of polyester dendrimers

• Published in: Tetrahedron Vol. 66; no. 50; pp. 9602 - 9609
• Main Authors: Twibanire, Jean-d’Amour K., Al-Mughaid, Hussein, Grindley, T. Bruce
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.12.2010; Elsevier
• Subjects: Anhydrides; Applied sciences; Chemistry; Chemistry, Organic; Dendrimers; Derivatives; Exact sciences and technology; Hydrogenolysis; Organic polymers; Physical Sciences; Physicochemistry of polymers; Polyester resins; Polymers with particular structures; Preparation, kinetics, thermodynamics, mechanism and catalysts; Science & Technology; Synthesis (chemistry); Terminals; Tetrahedrons; SURFACE-PROPERTIES; CONFORMATIONAL EQUILIBRIA; ETHERS; ACID; POLYOLS; CONSTRUCTION; ALLYLATION; BIOLOGICAL EVALUATION; DERIVATIVES; Molecular orbital; Ozonolysis; One pot reaction; End group; Ester polymer; Organic anhydride; Acetic anhydride; Allylic compound; Cis stereoisomer; Chemical reduction; Hydroxyl group; Chemical synthesis; Dendritic structure
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.10.018

Six dendrimer and dendron cores terminated by hydroxyl groups that are neither phenolic nor cleavable by hydrogenolysis have been prepared in a consistent one-pot manner from terminal allyl groups by reduction of the product of reductive ozonolysis. Some of the terminal allyl derivatives are new and others have been prepared by new methods. The well-known O-benzylidene derivative of 2,2′-bis(hydroxymethyl)propanoic acid was shown to be the cis-stereoisomer. A new AB 3-type anhydride, tris(benzyloxymethyl)acetic anhydride has been prepared. It was demonstrated that these cores and dendrons could be assembled into first and second generation homo- and mixed polyester dendrimers. [Display omitted]