THERMOLYSIS OF DICYCLOPENTADIENYLMETHYL ALCOHOLS - A NOVEL SYNTHESIS OF FULVENES

被引:1
作者
KUMAGAI, T [1 ]
OHNO, M [1 ]
MITANI, K [1 ]
YAMAMOTO, K [1 ]
ODA, M [1 ]
机构
[1] OSAKA UNIV, FAC SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
关键词
D O I
10.1246/bcsj.68.301
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thermolyses of isomeric mixtures of dicyclopentadienylmethyl alcohols were obtained by reactions of the corresponding isomeric mixture of metallodicyclopentadiene with aldehydes and ketones at 300 degrees C by a flow method. These thermolyses give by cycloreversion the corresponding isomeric mixtures of cyclopentadienyl-methyl alcohols. These mixtures in turn furnish the corresponding fulvenes upon treatment with bases. At higher temperatures, the thermolyses regenerate starting ketones, probably by retro-ene reaction of the cycloreversed alcohols.
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页码:301 / 304
页数:4
相关论文
共 8 条
[1]   RETRO-DIELS-ALDER REACTIONS .3. KINETICS OF THERMAL DECOMPOSITIONS OF EXO- AND ENDO-DICYCLOPENTADIENE [J].
HERNDON, WC ;
GRAYSON, CR ;
MANION, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :526-&
[2]  
KRESZE G, 1961, LIEBIGS ANN CHEM, V648, P57
[3]  
KRESZE G, 1961, LIEBIGS ANN CHEM, V648, P51
[4]   PREPARATIVE DERIVATIZATION OF ENDO-DICYCLOPENTADIENE VIA METALATION [J].
KUMAGAI, T ;
AGA, M ;
OKADA, K ;
ODA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (04) :1428-1430
[5]   TANDEM REACTIONS OF N,N-DIALKYLAMIDES WITH ORGANOLITHIUM COMPOUNDS AND CYCLOPENTADIENE - A NEW EFFICIENT SYNTHESIS OF PENTAFULVENES [J].
KURATA, H ;
EKINAKA, T ;
KAWASE, T ;
ODA, M .
TETRAHEDRON LETTERS, 1993, 34 (21) :3445-3448
[6]  
KURATA H, 1991, CHEM EXPRESS, V6, P853
[7]  
LLOYD D, 1984, NONBENZENOID CONJUGA, P46
[8]  
Zeller K. P., 1985, METHOD ORGAN CHEM, V5/2C, P504