102599-25-7Relevant articles and documents
Formation of Tetraacetal Oxa-Cages and Convex Oxa-Cages Ozonolysis of Bicyclooctenes
Lin, Chu-Chung,Wu, Hsien-Jen
, p. 815 - 820 (2007/10/03)
Tetraacetal oxa-cage compounds 5a and 5b and convex oxa-cage compounds 7a and 8a are synthesized in a short sequence.Ozonolysis of endo adducts 2a and 2b in dichloromethane at -78 deg C followed by reduction with dimethylsulfide gave tetraacetal oxa-cages 5a and 5b in 35percent yields respectively.Ozonolysis of 2a in dichloromethane at -78 deg C followed by treatment with triethylamine gave the convex oxa-cage 7a in 34percent 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 oxacage 14, possessing aromatic substitutents directly on the skeleton of the oxa-cage, is accomplished.Key Words: Tetraacetal oxa-cages; Convex oxa-cages; Ozonolysis; Bicyclooctenes.