Premium
First Total Synthesis and Structural Confirmation of C13‐Butylrubber Oligomers
Author(s) -
Minicone Fabrizio,
Attrill Robin,
Hodgson Michael,
Wheelhouse Katherine,
Dobbs Adrian
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800496
Subject(s) - oligomer , chemistry , total synthesis , polymer science , organic chemistry , combinatorial chemistry
The first total synthesis of an important C13 butyl rubber 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.