Abstract/Details

The study of methods to synthesize silylated calixarenes in the 1,3-alternate conformation


2009 2009

Other formats: Order a copy

Abstract (summary)

Calixarenes are macrocyclic compounds that have aromatic rings that are connected by methylene bridges. They are useful in both biological and chemical industries, as receptors, and in catalysis. Silylated calixarenes are of potential interest in molecular recognition. We investigated the synthesis of C-silylated calixarenes in the 1,3-alternate conformation. p-tert-Butylcalix[4]arene was dealkylated, and the 1,3-alternate conformation was established via the two-pot procedure of sequential treatment with propyl iodide/K2CO 3 followed by propyl tosylate/CsCO3. The corresponding bromocalixarene was prepared using NBS. Silylation was carried out via halogen-metal exchange using tert-BuLi, followed by the supernatant from a mixture of silylating reagent and Et3N. Calixarenes were prepared having the Me3Si, Me2PhSi, Me2HSi, and the Me 2(allyl)Si groups.

Although the halogen metal exchange reactions proved to be successful, the use of tert-BuLi reagents is impractical for large scale reactions. Therefore, we investigated new ways to synthesize silylated compounds. We studied the use of Mg reagents to make the silylated compounds. We used the monocyclic compound bromoanisole as a model for the new reactions before trying them on the calixarene. The results indicated that some of these reaction were successful on the model compound, but not on the calixarenes.

Indexing (details)


Subject
Organic chemistry
Classification
0490: Organic chemistry
Identifier / keyword
Pure sciences; Anion recognition; Calixarenes; Silylated calixarenes; Silylation
Title
The study of methods to synthesize silylated calixarenes in the 1,3-alternate conformation
Author
Tatum, Prima R.
Number of pages
120
Publication year
2009
Degree date
2009
School code
0088
Source
DAI-B 70/03, Dissertation Abstracts International
Place of publication
Ann Arbor
Country of publication
United States
ISBN
9781109079890
Advisor
Hudrlik, Paul F.
Committee member
Bakare, Oladapo; Butcher, Raymond J.; Hijji, Yousef M.; Matthews, Jason S.
University/institution
Howard University
Department
Chemistry
University location
United States -- District of Columbia
Degree
Ph.D.
Source type
Dissertations & Theses
Language
English
Document type
Dissertation/Thesis
Dissertation/thesis number
3350306
ProQuest document ID
304895904
Copyright
Database copyright ProQuest LLC; ProQuest does not claim copyright in the individual underlying works.
Document URL
http://search.proquest.com/docview/304895904
Access the complete full text

You can get the full text of this document if it is part of your institution's ProQuest subscription.

Try one of the following:

  • Connect to ProQuest through your library network and search for the document from there.
  • Request the document from your library.
  • Go to the ProQuest login page and enter a ProQuest or My Research username / password.