Heterotricyclodecane X . 2‐Oxa‐7‐thia‐isotwistan und 2‐Oxa‐7‐thia‐twistan sowie Derivate | Zendy

Wigger N. | Zendy; Ganter C. | Zendy

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Heterotricyclodecane X . 2‐Oxa‐7‐thia‐isotwistan und 2‐Oxa‐7‐thia‐twistan sowie Derivate

Author(s) -

Wigger N.,

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.19720550808

Subject(s) - chemistry , sulfonium , oxonium ion , iodide , bromide , medicinal chemistry , stereochemistry , ion , organic chemistry , salt (chemistry)

The synthesis of 2‐oxa‐7‐thia‐isotwistane ( 11 ) and 2‐oxa‐7‐thia‐twistane ( 22 ) as well as of several of their derivatives is described starting from endo ‐2‐hydroxy‐9‐thiabi cyclo[3.3.1]non‐6‐ene ( 4 ). The 10 O(2) ‐isotwistane bromide 13 , iodide 14 and tosylate 30 as well as the 10 S(7) ‐isotwistane iodide 15 , tosylate 20 , and the 10 S(7) ‐twistane tosylate 21 were treated under reaction conditions suitable for molecular rearrangements involving the epi ‐sulfonium ion i and the oxonium ion g . respectively, by neighbouring group participation.

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