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3‐Azawurtzitan und 3(4 → 5) abeo ‐3‐Azawurtzitan
Author(s) -
Klaus Rolf Otto,
Ganter Camille
Publication year - 1980
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.19800630851
Subject(s) - chemistry , intramolecular force , stereochemistry , ketone , amination , epoxide , olefin fiber , organic chemistry , catalysis , polymer
3‐Azawurtzitane and 3(4 → 5) abeo ‐3‐Azawurtzitane 3‐Azawurtzitane (14) and 3(4 → 5) abeo ‐3‐azawurtzitane (15) as well as derivatives thereof are described. The known tricyclic unsaturated ketone 1 was transformed to the properly functionalized endo ‐amines 3, 5 and 12. Entry to the azawurtzitane system and its corresponding abeo ‐compounds was achieved by three different cyclization procedures: aminomercuration with mercuric acetate in water (3 → 14, 5 → 16) , olefin amination with mercuric acetate in dimethyl sulfoxide (3 → 18, 5 → 20 + 21) and intramolecular attack at an epoxide (12 → 24 + 25). Molecular rearrangements of 3‐azawurtzitanes to 3(4 → 5) abeo ‐3‐azawurtzitanes and vice versa are described involving neighbouring group participation of the N (3) atom.