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Synthesis of large container molecules

University of British Columbia

This thesis presents the synthesis and guest binding abilities of a multitude of hosts derived from cavitand 37. In chapter 2, the mechanism of formation of hemicarceplex 60 guest using transition state models is discussed. This chapter includes reactions and complexation experiments with 61 (R¹ = R² = H) and its derivatives in Nformylpiperidine (NFP) and nitrobenzene. The formation of tris-carceplex 75«(methyl acetate^ and tris-capsule 76«(methyl acetate)3 from hexamer 74 is discussed in chapter 3. In chapter 4, we present the formation and guest binding abilities of hosts 78 and 81. The guest decomplexation rate of 78«(l,3,5-triethynylbenzene)2 is also discussed. In chapter 5, we discuss the entrapment and the reaction of PI1COCHN2 to produce PhCHC=C=0 within the cavity of 45. In situ generation of l,3,5-tris(iodomethyl)benzene, and its entrapment within the cavity 152 are described. The stability of bound l,3,5-tris(iodomethyl)benzene is also discussed.

Thesis/Dissertation

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2009-11-17

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http://hdl.handle.net/2429/15109

Chemistry

University of British Columbia

UBCV

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