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Substituierte 9‐Oxabicyclo[4.2.1]‐ und 9‐Oxabicyclo[3.3.1]nonane III. neue ergiebige synthese von 2, 7‐dioxatwistan und endo ‐2‐hydroxy‐9‐oxabicyclo[3.3.1]nonen‐(6)
Author(s) -
Ganter C.,
Zwahlen W.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540826
Subject(s) - chemistry , dehydrohalogenation , nonane , iodine , intramolecular force , stereochemistry , medicinal chemistry , iodide , organic chemistry , catalysis
Iodine cleavage of the [3.3.1]‐iodomercuri compound 4 , easily prepared from cis , cis ‐cyclooctadiene‐(1,5) by oxymercuration of the monoepoxide 1 (→ 3 ) followed by treatment with potassium iodide, leads to three isomeric iodides 6, 7 , and 8 , the [3.3.1]‐ exo ‐iodo isomer 8 being the predominant product. Intramolecular substitution in 8 opens an attractive new route to unsubstituted 2,7‐dioxatwistane ( 19 ) [2], whereas dehydrohalogenation of 7 and 8 yields the unsaturated alcohol 17 [2], a suitable starting material for the preparation of substituted 2,7‐dioxatwistanes [2], 2,7‐dioxaisotwistanes ( e ) [2], and 2,8‐dioxa‐homotwistbrendanes ( f ).