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Formation of Tetraacetal Oxa‐Cages and Convex Oxa‐Cages on Ozonolysis of Bicyclo[2.2.2] Octenes
Author(s) -
Lin ChuChung,
Wu HsieiiJen
Publication year - 1995
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199500110
Subject(s) - chemistry , ozonolysis , cage , dichloromethane , triethylamine , yield (engineering) , adduct , base (topology) , medicinal chemistry , stereochemistry , solvent , organic chemistry , mathematical analysis , materials science , mathematics , combinatorics , metallurgy
Tetraacetal oxa‐cage compounds 5a and 5b and convex oxa‐cage compounds 7a and 8b are synthesized in a short sequence. Ozonolysis of endo adducts 2a and 2b in dichloromethane at −78 °C followed by reduction with dimethylsulfide gave tetraacetal oxa‐cages 5a and 5b in 35% yields respectively. Ozonolysis of 2a in dichloromethane at −78 °C followed by treatment with triethylamine gave the convex oxa‐cage 7a in 34% yield. These results support an acid‐base proton transfer between the final ozonides and the base. The reasons that these oxa‐cage compounds formed in low yields are discussed. The synthesis of tetraacetal oxa‐cage 14, possessing aromatic substitutents directly on the skeleton of the oxa‐cage, is accomplished.