Abstract
3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves π-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes.
Original language | English |
---|---|
Pages (from-to) | 1426-1429 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 13 |
DOIs | |
State | Published - 2011/03/30 |
Keywords
- Cycloaddition
- Electrocyclic reaction
- Enamine
- Methanothia-annulene
- X-ray crystallographic analysis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry