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Eine einheitlich verlaufende aliphatische Benzilsäure‐Typ‐Umlagerung
Author(s) -
Schaltegger Alexander,
Bigler Peter
Publication year - 1986
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.19860690721
Subject(s) - chemistry , benzil , oxidative cleavage , isomerization , medicinal chemistry , bond cleavage , ring (chemistry) , enone , wolff rearrangement , aqueous solution , organic chemistry , catalysis , ketene
An Uniformly Occurring Aliphatic Benzil‐Benzilic‐Acid‐Type Rearrangement Treatment of 6‐bromo‐2,2,5,5‐tetramethylcyclohex‐3‐enone ( 2 ) with aqueous alkaline and air affords 1‐hydroxy‐2,2,5,5‐tetramethylcyclopent‐3‐enecarboxylic acid ( 8 ) as the major product of a benzil‐benzilic‐acid‐type rearrangement. The key compound is 2,2,5,5‐tetramethylcyclohex‐3‐ene‐1,2‐dione ( 11 ). The by‐product of the reaction is ( E )‐2,2,5,5‐tetramethylhex‐3‐enedioic acid ( 9 ) as the result of an oxidative cleavage of the 6‐membered ring and the isomerization of the double bond.