AI Article Synopsis
- Cyclotriguaiacylene is a key precursor for cryptophanes and helps in making specialized cavitands from the cyclotriveratrylene family.
- Its thio analogue, cyclotrithioguaiacylene, was produced using two methods: Newman-Kwart and Pummerer rearrangements.
- The Pummerer rearrangement, using a trisulfoxide precursor, resulted in a cleaner product with a higher overall yield.
Article Abstract
Cyclotriguaiacylene 1 is the universal precursor of cryptophanes, and represents an important intermediate for the preparation of functionalized cavitands of the cyclotriveratrylene family. Its thio analogue (cyclotrithioguaiacylene 3) was synthesized by two different routes, involving either the Newman-Kwart or the Pummerer rearrangement. The latter, performed starting from a trisulfoxide precursor, produced a purer compound in higher overall yield.
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| http://dx.doi.org/10.1021/jo102324u | DOI Listing |
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Sulfur-incorporating cyclotriveratrylene analogues: the synthesis of cyclotrithioguaiacylene.
J Org Chem
March 2011
Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB, CNRS UMR no. 5260), 9 Avenue Alain Savary, BP 47870, F-21078 Dijon, France.
Article Synopsis
- Cyclotriguaiacylene is a key precursor for cryptophanes and helps in making specialized cavitands from the cyclotriveratrylene family.
- Its thio analogue, cyclotrithioguaiacylene, was produced using two methods: Newman-Kwart and Pummerer rearrangements.
- The Pummerer rearrangement, using a trisulfoxide precursor, resulted in a cleaner product with a higher overall yield.
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