Return to search

Cycloaromatization reactions of enamines

Methyl 4-trimethylsilyl-3-dialkylaminocrotonate is synthesized by the silylation of methyl 3-dialkylaminocrotonate. It reacts with carbonyl electrophiles at its (gamma)-position. The unusual regiochemistry of this reaction is studied and rationalized. It reacts with enamines derived from acyclic ketones or cycloketones of large ring size (of 12 and 15 membered rings) to give aromatic compounds in a 3C + 3C combination and with enamines derived from cycloketones of 5-8 membered rings to give aromatic compounds in a 4C + 2C combination. The mechanism of this cycloaromatization reaction is investigated. / meta-Cyclophanes with a morpholino substituent are synthesized by the above cycloaromatization reaction. These meta-cyclophanes possess planar chirality and are successfully resolved. / A number of metacyclophanes with alkyl substituents at the intraannular position are synthesized. Depending on the ring size and the steric size of the alkyl group, some of them are also resolved. The rotation process of meta-cyclophane is studied through their temperature dependent ('1)H NMR.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71883
Date January 1983
CreatorsKang, Guo-jun.
PublisherMcGill University
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Formatapplication/pdf
CoverageDoctor of Philosophy (Department of Chemistry.)
RightsAll items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated.
Relationalephsysno: 000195035, proquestno: AAINK66620, Theses scanned by UMI/ProQuest.

Page generated in 0.0019 seconds