GAMMA,GAMMA-DISUBSTITUTED ITACONIC ACIDS .1. STOBBE CONDENSATION OF 1-ARYLNAPHTHYL KETONES WITH DIETHYL SUCCINATE

被引:8
作者
BAGHOS, VB
NASR, FH
GINDY, M
机构
[1] Department of Chemistry, Faculty of Science, Cairo University, Cairo
关键词
D O I
10.1002/hlca.19790620114
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Arylnaphthyl ketones condense with diethyl succinate yielding the stereoisomeric half‐esters 2a–2d which were subjected to a series of reactions leading to 1‐phenylphenanthrene and 1,1′‐binaphthyl derivatives. (E)‐3‐Ethoxycarbonyl‐4‐(4‐methoxynaphth‐1‐yl)‐4‐arylbut‐3‐enoic acids (2b–d) were converted finally into the corresponding naphtho[1,2‐c]fluorenones (9). The structure of the products was established by IR. and UV. spectroscopy. The effect of substituents on the relative proportions of (E)‐ and (Z)‐half‐esters 2 was determined by chromatography and UV. spectroscopy. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim
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页码:90 / 100
页数:11
相关论文
共 10 条
[1]   GAMMA GAMMA-DISUBSTITUTED ITACONIC ACIDS .2. CONVERSION OF BETA-ETHYL ALPHA-HYDROGEN GAMMA-ALPHA-NAPHTHYL-GAMMA-PHENYLITACONATE INTO 1-METHOXY-4-PHENYLPHENANTHRENE AND 7-METHOXYNAPHTHO[C-Z,1]FLUOREN-9-ONE [J].
AWAD, WI ;
SELIM, MIB ;
BADDAR, FG .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAY) :1854-&
[2]   GAMMAGAMMA-DISUBSTITUTED ITACONIC ACIDS .4. STOBBE CONDENSATION OF 6-BENZOYLTETRALIN AND 2-BENZOYLNAPHTHALENE WITH DIETHYL SUCCINATE [J].
AWAD, WI ;
BADDAR, FG ;
FOULI, FA ;
OMRAN, SMA ;
SELIM, MIB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05) :507-&
[3]   1-PHENYLNAPHTHALENES .4. THE CYCLISATION OF METHYL HYDROGEN CIS AND TRANS-GAMMA-ORTHO-METHOXYPHENYL AND ETHYL HYDROGEN CIS AND TRANS-GAMMA-PARA-METHOXYPHENYL-GAMMA-PHENYLITACONATE TO THE CORRESPONDING 1-PHENYLSTEREOCHEMISTRY [J].
BADDAR, FG ;
ELASSAL, LS ;
BAGHOS, VB .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAR) :986-994
[4]  
BADDAR FG, 1975, J INDIAN CHEM SOC, V52, P1177
[5]  
BELLAMY LJ, 1958, INFRARED SPECTRA COM, P145
[6]   THE PREPARATION OF POLYCYCLIC AROMATIC HYDROCARBONS FROM ARYLPROPIOLIC ACIDS [J].
CAMPBELL, AD .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (NOV) :3659-3669
[7]   ELECTROPHILIC SUBSTITUTION .8. THE NITRATION OF DIBENZOFURAN AND A NEW METHOD OF ULTRAVIOLET SPECTROPHOTOMETRIC ANALYSIS OF MIXTURES [J].
DEWAR, MJS ;
URCH, DS .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JAN) :345-347
[8]   4-Alkyl Derivatives of 1,2-Naphthoquinone [J].
Fieser, LF ;
Bradsher, CK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1939, 61 :417-423
[9]   BENZO[C]FLUORENONES .3. CONVERSION OF 4,4-DISUBSTITUTED 3-ALKOXYCARBONYLBUT-3-ENOIC ACIDS INTO BENZO[C]FLUORENONE DERIVATIVES [J].
GINDY, M ;
BAGHOS, VB ;
SHABAN, AM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (14) :1905-+
[10]  
SILLAM, 1955, INTRO ELECTRONIC ABS, P245