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Studies on the Himbert Intramolecular Arene/ Allene Diels – Alder Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon Tethers
- Publication Year :
- 2013
-
Abstract
- The unusual intramolecular arene/allene cycloaddition described thirty years ago by Himbert permits rapid access to strained polycyclic compounds that offer great potential for the synthesis of complex scaffolds. To more fully understand the mechanism of this cycloaddition reaction, and to guide efforts to extend its scope to new substrates, quantum mechanical computational methods were employed in concert with laboratory experiments. These studies indicated that the cycloadditions likely proceed via concerted processes; a stepwise biradical mechanism was shown to be higher in energy in the cases studied. The original Himbert cycloaddition chemistry is also extended from heterocyclic to carbocyclic systems, with computational guidance used to predict thermodynamically favorable cases. Complex polycyclic scaffolds result from the combination of the cycloaddition and subsequent ring-rearrangement metathesis reactions.
- Subjects :
- Models, Molecular
Scope (project management)
Cycloaddition Reaction
Chemistry
Allene
chemistry.chemical_element
General Chemistry
Biochemistry
Catalysis
Cycloaddition
Article
Carbon
Alkadienes
chemistry.chemical_compound
Colloid and Surface Chemistry
Computational chemistry
Mechanism (philosophy)
Intramolecular force
Salt metathesis reaction
Diels alder
Organic chemistry
Polycyclic Compounds
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....c95ec48995f89965159ec9303eaec9f0