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Directed Ortho Metallation of Deep Cavity Cavitands: Functionalizing Molecular Concavity

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Zachary R. Laughrey and Bruce C. Gibb*

Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148

J. Org. Chem., 2006, 71 (4), pp 1289–1294

DOI: 10.1021/jo0513515

Publication Date (Web): October 12, 2005

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Abstract

Directed ortho metallation (DOM) processes have been used to functionalize the cavity and rim of title cavitand 1. The preorganization of the host resulted in a considerable reduction in the range of products produced. Thus, whereas sixty-nine products are possible from per-functionalization, only twelve were observed when the host was treated with three different alkyllithiums.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Electrophilic Substitution of Deep Cavity Cavitands: Selective Exo Functionalization of Molecular Concavity
Kannupal Srinivasan and Bruce C. Gibb
Organic Letters2007 9 (5), 745-748
- Electrophilic Substitution of Deep Cavity Cavitands: Selective Exo Functionalization of Molecular Concavity
  Kannupal Srinivasan and Bruce C. Gibb
  Organic Letters2007 9 (5), 745-748
  The functionalization of deep-cavity cavitands via electrophilic substitution was investigated. In the parent structures, substitution occurs both at the exo position of the bowl-shaped hosts and on the convex face. Little or no endo substitution was ...
  Abstract | Full Text HTML | Hi-Res PDF
Templated Assembly of Water-Soluble Nano-Capsules: Inter-Phase Sequestration, Storage, and Separation of Hydrocarbon Gases
Corinne L. D. Gibb and Bruce C. Gibb
Journal of the American Chemical Society2006 128 (51), 16498-16499
- Templated Assembly of Water-Soluble Nano-Capsules: Inter-Phase Sequestration, Storage, and Separation of Hydrocarbon Gases
  Corinne L. D. Gibb and Bruce C. Gibb
  Journal of the American Chemical Society2006 128 (51), 16498-16499
  In aqueous solution, a deep-cavity cavitand was shown to self-assemble into dimeric nano-capsules via the sequestration of gaseous-phase hydrocarbons. The sequestration, assembly, and entrapment process was shown to be dependent on the hydrocarbon. Thus, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links