Synthesis, structure and unusual reactivity of a stable 3-(oxazolidin-2-ylidene)thiophen-2-one
Date
04/11/2016Metadata
Show full item recordAbstract
Treatment of 2- and 3-thienyloxazolines with butyllithium and bis(trimethylsilyl) peroxide results in ring hydroxylation to give products which exist mainly as the oxazolidinylidenethiophenones. The 3-oxazolidinylidenethiophen-2-one is a rare example of a stable heterocyclic ortho-quinone methide analog which shows a varied pattern of reactivity, including both C- and O-alkylation, Michael addition via C-5 to an acetylenic ester, tetrachlorobenzannulation across positions 4 and 5, and formation of a hexacyclic fused-ring product with N-phenyltriazolinedione. Crystal structures of the products are dominated by inter- and intramolecular NH to CO hydrogen bonding.
Citation
Aitken , R A , Harper , A D & Slawin , A M Z 2016 , ' Synthesis, structure and unusual reactivity of a stable 3-(oxazolidin-2-ylidene)thiophen-2-one ' , The Journal of Organic Chemistry , vol. 81 , no. 21 , pp. 10527-10531 . https://doi.org/10.1021/acs.joc.6b01309
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
ISSN
0022-3263Type
Journal article
Description
The authors thank EPSRC (UK) for a DTA studentship (Grant EP/L505079/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University.Collections
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