Studies on Cage Compounds. Synthesis of 8,11‐Diazenediyl‐4,4‐Dimethoxy‐2,3,5,6‐Tetrachloropentacyclo[5.4.0.0 2,5 .0 3,10 .0 5,9 ]Undecane | Zendy

Chou TehChang | Zendy; Chiou JongHsin | Zendy

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Studies on Cage Compounds. Synthesis of 8,11‐Diazenediyl‐4,4‐Dimethoxy‐2,3,5,6‐Tetrachloropentacyclo[5.4.0.0 2,5 .0 3,10 .0 5,9 ]Undecane

Author(s) -

Chou TehChang,

Chiou JongHsin

Publication year - 1986

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.198600030

Subject(s) - chemistry , adduct , decarboxylation , diene , yield (engineering) , hydrolysis , derivative (finance) , diethyl azodicarboxylate , medicinal chemistry , cage , stereochemistry , organic chemistry , catalysis , triphenylphosphine , natural rubber , materials science , mathematics , combinatorics , economics , financial economics , metallurgy

The title compound ( 7 ) was synthesized in six steps from 1,8,9,10‐tetrachloro‐11,11‐dimethoxy‐ endo ‐tricyclo[6.2.1.0 2,7 ]undeca‐4,9‐diene‐3,6‐dione ( 4 ) in an overall yield of 36%. The key intermediate, 1,8,9,10‐tetrachloro‐11,11‐dimethoxy‐ endo ‐tricyclo‐[6.2.1.0 2,7 ]undeca‐3,5,9‐triene ( 12 ), obtained from 4 by reduction, mesylation and then 1,4‐elimination, was allowed to react with diethyl azodicarboxylate to afford the Diels‐Alder adduct 16 . Photochemical closure of 16 , followed by hydrolysis and decarboxylation, gave the title compound. The title compound failed to give either the homopentaprismanone derivative 3 or the diene 9 by the photochemical or thermal elimination of molecular nitrogen.

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