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Synthesis of 3,5,7‐Trioxapentacyclo[7.2.1.0 2,8 .0 4,11 .0 6,10 ]dodecane. A Novel Diacetal Trioxa‐Cage
Author(s) -
Tsai ShihHwa,
Wu HsienJen,
Chung WenSheng
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.199600064
Subject(s) - chemistry , dodecane , adduct , maleic anhydride , yield (engineering) , ozonolysis , cyclopentadiene , medicinal chemistry , stereochemistry , nuclear chemistry , organic chemistry , polymer , materials science , metallurgy , copolymer , catalysis
3,5,7‐Trioxapentacyclo[7.2.1.0 2,8 .0 4,11 .0 6,10 ]dodecane, the parent compound of novel diacetal trioxa‐cages, was synthesized from maleic anhydride cyclopentadiene adduct 1 by a four‐step sequence. Attempts for the synthesis of monoaza dioxa‐cage 12 failed. Ozonolysis of compound 9 in CH 2 Cl 2 ‐EtOH(1:1) at −78°C followed by reduction with Me 2 S gave 13 in 65% yield.