Eine umlagerung  S ‐substituierter cyclohexanonthioxime | Zendy

Andreae Siegfried | Zendy; Schmitz Ernst | Zendy; Schulz Burkhard | Zendy

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Eine umlagerung S ‐substituierter cyclohexanonthioxime

Author(s) -

Andreae Siegfried,

Schmitz Ernst,

Schulz Burkhard

Publication year - 1994

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199419940211

Subject(s) - chemistry , cyclohexanone , ketene , octane , medicinal chemistry , hydrolysis , nitrogen atom , carbon atom , organic chemistry , stereochemistry , ring (chemistry) , catalysis

A Rearrangement of S ‐Substituted Cyclohexanone Thioximes Mercaptoheterocycles like 2‐mercaptobenzazoles 5 , 2‐mercaptouracils 10 , and ketene S,S‐acetals 18 are aminated by 1‐oxa‐2‐azaspiro[2.5]octane ( 1 ). The intermediate cyclohexanone thioximes, which can be isolated in some cases ( 6a–c, 11 ), undergo a 1,3‐shift of the mercapto fragment from the nitrogen to the carbon atom followed by cyclization and/or hydrolysis. Thus, new heterocyclic systems as 14–17 or 19 can be created.

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