Skip navigation

First total synthesis and structural confirmation of C13-Butylrubber Oligomers

First total synthesis and structural confirmation of C13-Butylrubber Oligomers

Minicone, Fabrizio, Attrill, Robin, Hodgson, Michael, Wheelhouse, Katherine and Dobbs, Adrian (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)

[img] PDF (Author Accepted Manuscript)
20537 DOBBS_First_Total_Synthesis_and_Structural_Confirmation_2018.pdf - Accepted Version
Restricted to Repository staff only until 29 June 2019.

Download (524kB) | Request a copy

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 / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
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:
Last Modified: 20 May 2019 13:32
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
URI: http://gala.gre.ac.uk/id/eprint/20537

Actions (login required)

View Item View Item

Downloads

Downloads per month over past year

View more statistics