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Conjugated Unsaturated Ketones. XIII. A Side‐Reaction in the Preparation of Dibenzylidenecyclohexanone and Thermal Isomerization and Dimerization of Dibenzylidenecyclohexanone

 

作者: Ping‐Yuan Yeh,   Chao‐Tung Chen,   Cheng‐Hsia Wang,   Pik‐Kuei Chang,   Shu Shu Yang,  

 

期刊: Journal of the Chinese Chemical Society  (WILEY Available online 1957)
卷期: Volume 4, issue 1‐2  

页码: 82-104

 

ISSN:0009-4536

 

年代: 1957

 

DOI:10.1002/jccs.195700010

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

Abstract9‐Phenyl‐1,2,3,4,5,6,7,8‐octahydrodibenzo‐γ‐pyran (V) was obtained from the mother liquor of crude 2,6‐dibenzylidenecyclohexanone (DBH) (1).Oxidation of 2,5‐dibenzylidenecyclopentanone (DBP) and DBH yielded benzoic and succinic acids, and benzoic, glutaric and 2‐benzylideneadipic acids respectively. Chromic acid oxidation of DBH gave benzaldehyde and benzoic acid, while that of the DBH dimer did not yield either of the two products.The formation of the DBH dimer by refluxing DBH in ethanol was inhibited by acid, alkali, rubber stopper, and sulfur, but was not affected by soft glasswares.Two dimers and three monomeric isomers of DBH were isolated, two of them probably represent cis forms.Thermal isomerization and dimerization of dibenzylideneacetone, difurfurylideneacetone, and difurfurylidenecyclohexanone were also studied. The latter two compounds were failed to give even a trace of the expected isomers or dimers.DBH gave, with phenylhydrazine, 2,3‐diphenyl‐7‐benzylidenecyclohexa‐pyrazoline (XII), while DBP with the same reagent at 190‐200° afforded benzaldehyde phenylhdrazone, ammonia, and water. The tetra‐bromide of DBP (XV) and phenylhydrazine readily gave

 

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