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Heterotricyclodecane IX . 2, 7‐Dioxa‐isotwistan, 2, 7‐Dioxatwistan und 2, 8‐Dioxa‐homotwistbrendan sowie Derivate
Author(s) -
Wicker K.,
Ackermann P.,
Ganter C.
Publication year - 1972
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.19720550807
Subject(s) - oxonium ion , chemistry , iodide , medicinal chemistry , ion , stereochemistry , organic chemistry
The synthesis of 2, 7‐dioxa‐isotwistane ( 10 ), 2, 7‐dioxa‐twistane ( 17 ), and 2, 8‐dioxa‐homotwistbrendane ( 36 ) and several of their derivatives is described starting from endo ‐2‐hydroxy‐9‐oxabicyclo[3.3.1]non‐6‐ene ( 1 ). The 10 O(7) ‐isotwistane iodide 7 and the corresponding tosylate 15 as well as the 10 O(2) ‐iodide 9 were treated under reaction conditions suitable for molecular rearrangements involving oxonium ions g and i , respectively, by neighbouring group participation leading to 2, 7‐dioxa‐twistanes and 2, 8‐dioxa‐homotwistbrendanes, respectively.