Minicone, Fabrizio, Attrill, Robin, Hodgson, Michael, Wheelhouse, Katherine and Dobbs, Adrian ORCID: 0000-0002-7241-7118 (2018) First total synthesis and structural confirmation of C13-Butylrubber Oligomers. European Journal of Organic Chemistry, 2018 (25). pp. 3271-3275. ISSN 1434-193X (Print), 1099-0690 (Online) (doi:https://doi.org/10.1002/ejoc.201800937)

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Abstract

The first total synthesis of an important C13 butylrubber oligomer is reported. The structure of the oligomer, which is an important and potentially toxic extractable and leachable component of elastomeric closures, is confirmed by synthesis for the first time. The method described is scalable, making large quantities of the oligomer available for the first time for AMES toxicity studies. The challenging synthesis commences with isophorone and the key steps of the synthesis involve the development of highly novel dithoacetal chemistry, cuprate addition and Tebbe olefination.

Item Type:	Article
Uncontrolled Keywords:	Elastomer; Oligomer; Total synthesis; Structure elucidation; Isophorone; Tebbe reagent; Hydrogenation
Subjects:	Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI) Faculty of Engineering & Science > Medway Centre for Pharmaceutical Science Faculty of Engineering & Science > Medway Centre for Pharmaceutical Science > Pharmaceutical and Medicinal Science Research Group
Related URLs:	Publisher
Last Modified:	21 Oct 2020 22:31
URI:	http://gala.gre.ac.uk/id/eprint/20537

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