R. Aitken, Andrew D. Harper, A. Slawin
Jul 28, 2016
Citations
0
Influential Citations
4
Citations
Journal
The Journal of organic chemistry
Abstract
Treatment of 2- and 3-thienyloxazolines with butyllithium and bis(trimethylsilyl) peroxide results in ring hydroxylation to give products that exist mainly as the oxazolidinylidenethiophenones. The 3-oxazolidinylidenethiophen-2-one is a rare example of a stable heterocyclic o-quinone methide analogue that 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.