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Synthesis of Novel Triacetal Trioxa‐Cage Compounds by Ozonolysis of Bicyclo[2.2.1]Heptenes and Bicyclo[2.2.2]Octenes
Author(s) -
Wu ChungYi,
Lin ChuChung,
Lai MingCheng,
Wu HsienJen
Publication year - 1996
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.199600027
Subject(s) - ozonolysis , chemistry , bicyclic molecule , dichloromethane , cage , medicinal chemistry , bridged compounds , stereochemistry , organic chemistry , solvent , mathematics , combinatorics
Several novel triacetal trioxa‐cage compounds 11a‐11g, 13, 15, 17 and 19 are synthesized in a short sequence. Ozonolysis of bicyclo[2.2.1]heptenes 4a‐4c, 8a‐8c, 10a, 10b and 14 in dichloromethane at −78 °C followed by reduction with dimethyl sulfide gave triacetal oxa‐cages 11a‐11g, 13 and 15 in moderate yields, respectively. Ozonolysis of bicyclo[2.2.2]octenes 16 and 18 under the same reaction conditions gave triacetal oxa‐cages 17 and 19 in moderate yields, respectively.