Intramolecular acylation of aryl- and aroyl-aliphatic acids by the action of pyrophosphoryl chloride and phosphorus oxychloride

被引:19
作者
El-Sayrafi, S [1 ]
Rayyan, S [1 ]
机构
[1] Birzeit Univ, Dept Chem, Birzeit, Israel
关键词
pyrophosphoryl chloride; phosphorus oxychloride; cyclodehydration; cyclic ketones; anthraquinones;
D O I
10.3390/60300279
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Both pyrophosphoryl chloride and phosphorus oxychloride react: with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroyl-benzoic acids could be cyclized to the corresponding anthrones and anthraquinones respectively.
引用
收藏
页码:279 / 286
页数:8
相关论文
共 17 条
[11]   Syntheses of alkylphenanthrenes. Part I. 1-, 2-, 3-, and 4-methylphenanthrenes. [J].
Haworth, RD .
JOURNAL OF THE CHEMICAL SOCIETY, 1932, :1125-1133
[12]   ACYLIMINIUM IONS DERIVED FROM THE REARRANGEMENT OF BISCHLER-NAPIERALSKI CYCLIZATION PRODUCTS [J].
HEANEY, H ;
SHUHAIBAR, KF .
TETRAHEDRON LETTERS, 1994, 35 (17) :2751-2752
[13]   ENERGY DIFFERENCE BETWEEN CHAIR AND BOAT FORMSOF CYCLOHEXANE - TWIST CONFORMATION OF CYCLOHEXANE [J].
JOHNSON, WS ;
FRISCH, MA ;
BAUER, VJ ;
DREGER, LH ;
MARGRAVE, JL ;
HUBBARD, WN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (03) :606-+
[15]  
MEYER KH, 1941, ORG SYNTH, V1, P60
[16]   On the hydration of phenanthrene (II. Announcement). [J].
Schroeter, G ;
Muller, H ;
Huang, JYS .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1929, 62 :645-658
[17]   NEW SYNTHESIS OF 4-HYDROXYCOUMARINS [J].
SHAH, VR ;
BOSE, JL ;
SHAH, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) :677-678