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Synthese von Bicyclo[3.3.o]oct‐1(5)en‐2‐on aus Cyclohexanon
Author(s) -
LorenziRiatsch Annalaura,
Nakashita Yoshihiko,
Hesse Manfred
Publication year - 1984
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.19840670131
Subject(s) - chemistry , bicyclic molecule , yield (engineering) , cyclohexanone , medicinal chemistry , diketone , organic chemistry , catalysis , materials science , metallurgy
Synthesis of Bicyclo[3.3.0]oct‐1(5)en‐2‐one from Cyclohexanone Treatment of 2‐nitrocyclohexanone ( 2 ) with acrylaldehyde yielded in the presence of tetrabutylammonium fluoride the bicyclic product 5 , which was oxidized to the nitro‐diketone 3 . The conversion of 3 to the title compound 1 was achieved in the nearly quantitative yield under unusual conditions: K 2 CO 3 /H 2 O and H 2 SO 4 . Compound 3 , was also converted to 1 (stepwise and one‐pot reaction, respectively) by treatment with 1. NaOCH 3 , 2. TiCl 3 , and 3. H 2 SO 4 ( Scheme ).