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Tricyclo[3.1.0.0 2,6 ]hexanedione (the Valene of o ‐Benzoquinone), Bicyclo[2.1.1]hexane‐2,3‐dione, and Valenes of a Quinoxaline, of Phenazine, and of a Benzophenazine
Author(s) -
Christl Manfred,
Kraft Arno
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198813691
Subject(s) - phenazine , chemistry , quinoxaline , bicyclic molecule , hexane , swern oxidation , medicinal chemistry , benzoquinone , stereochemistry , organic chemistry , dimethyl sulfoxide
The Swern oxidation is ideal for the transformation of strained cis ‐1,2‐cyclo‐pentanediols such as 1 to α‐diketones such as 2 . Compound 2 , the valene of o ‐benzoquinone, is thus readily accessible. Its synthetic potential is demonstrated by the construction of other valenes, such as 3 (reaction of 2 with diaminomaleonitrile).