Heterotricyclodecane XVI . 2‐Oxa‐7‐aza‐isotwistane und 2‐Oxa‐7‐aza‐twistane | Zendy

Portmann Robert Ernst | Zendy; Ganter Camille | Zendy

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Heterotricyclodecane XVI . 2‐Oxa‐7‐aza‐isotwistane und 2‐Oxa‐7‐aza‐twistane

Author(s) -

Portmann Robert Ernst,

Ganter Camille

Publication year - 1973

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.19730560620

Subject(s) - chemistry , oxonium ion , bicyclic molecule , stereochemistry , olefin fiber , medicinal chemistry , ion , organic chemistry , catalysis

The synthesis of several derivatives of 2‐oxa‐7‐aza‐isotwistane ( 20–29 and 35 ) and 2‐oxa‐7‐twistane ( 30–34 ) is described starting from cis , cis ‐cycloocta‐1, 5‐diene ( 1 ). The bicyclic acetoxy‐olefin 10 was used as a key intermediate. The 10 N(7) ‐isotwistane 22 was treated under reaction conditions suitable for molecular rearrangements involving an oxonium ion g , by neighbouring group participation, leading to 2‐oxa‐7‐aza‐twistanes.

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