Synthesis of 3,5,7‐Trioxapentacyclo[7.2.1.0 2,8 .0 4,11 .0 6,10 ]dodecane. A Novel Diacetal Trioxa‐Cage | Zendy

Tsai ShihHwa | Zendy; Wu HsienJen | Zendy; Chung WenSheng | Zendy

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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.

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