Heterotricyclodecane IX . 2, 7‐Dioxa‐isotwistan, 2, 7‐Dioxatwistan und 2, 8‐Dioxa‐homotwistbrendan sowie Derivate | Zendy

Wicker K. | Zendy; Ackermann P. | Zendy; Ganter C. | Zendy

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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.

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