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3H-Pyrroles from ketoximes and acetylene: synthesis, stability and quantum-chemical insight.
- Source :
-
Tetrahedron . May2015, Vol. 71 Issue 21, p3273-3281. 9p. - Publication Year :
- 2015
-
Abstract
- Rare nonaromatic 3 H -pyrroles have been synthesized from ketoximes having only one CāH bond adjacent to the oxime function and acetylene under pressure (10ā13 atm) at 70 °C in two-phase superbase media of KOH/DMSO/ n -hexane type, the yields ranging 8ā36%. The effect of substituents, superbase nature and reaction conditions on yields of the target 3 H -pyrroles has been analyzed. Hydroxypyrroline/3 H -pyrroles interconversion as well as relative stability of model 3 H -pyrroles have been assessed quantum chemically (MP2/6-31++G**//B3LYP/6-31G**). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 71
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 102454756
- Full Text :
- https://doi.org/10.1016/j.tet.2015.03.111