SULFURATED GRIGNARD-REAGENT EQUIVALENT TO THAT OF 2-CHLOROMETHYL-1,3-BUTADIENE - NEW SYNTHESES OF IPSENOL "(2-METHYL-6-METHYLENE-7-OCTEN-4-OL) AND OF (E)-BETA-FARNESENE ((E)-7,11-DIMETHYL-3-METHYLENE-1,6,10-DODECATRIENE)

被引:15
作者
CAZES, B [1 ]
GUITTET, E [1 ]
JULIA, S [1 ]
RUEL, O [1 ]
机构
[1] ECOLE NORM SUPER,CNRS,CHIM LAB,EQUIPE RECH 12,F-75231 PARIS 5,FRANCE
关键词
D O I
10.1016/S0022-328X(00)92332-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Experiments on the synthesis of (3-methylene-4-chloro)butylphenyl sulfide, which is the precursor of the corresponding Grignard reagent, are described. With two typical electrophiles, namely isovaleraldehyde and geranyl chloride, this reagent provides the title terpenes in two further simple steps (oxidation to sulfoxides and thermolysis). © 1979.
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页码:67 / 74
页数:8
相关论文
共 30 条
[1]  
AKAIYAMA S, 1973, TETRAHEDRON LETT, P4115
[2]   METAL-ASSISTED TERPENOID SYNTHESIS .5. CATALYTIC TRIMERIZATION OF ISOPRENE TO TRANS-BETA-FARNESENE AND ITS SYNTHETIC APPLICATIONS FOR TERPENOIDS [J].
AKUTAGAWA, S ;
TAKETOMI, T ;
KUMOBAYASHI, H ;
TAKAYAMA, K ;
SOMEYA, T ;
OTSUKA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (04) :1158-1162
[3]  
BAKUZIS P, 1978, TETRAHEDRON LETT, P2371
[4]  
BERTRAND M, 1978, TETRAHEDRON LETT, P2575
[5]   APHID ALARM PHEROMONE - ISOLATION, IDENTIFICATION, SYNTHESIS [J].
BOWERS, WS ;
WEBB, RE ;
NAULT, LR ;
DUTKY, SR .
SCIENCE, 1972, 177 (4054) :1121-&
[6]  
BURGER BV, 1978, TETRAHEDRON LETT, P5221
[7]  
CARDILLO G, 1974, TETRAHEDRON LETT, P2215
[8]  
CARLSON RM, 1978, TETRAHEDRON LETT, P111
[9]   VINYL-LITHIUM REAGENTS FROM ARENESULFONYLHYDRAZONES [J].
CHAMBERLIN, AR ;
STEMKE, JE ;
BOND, FT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :147-154
[10]  
CLINET JC, 1977, NOUV J CHIM, V1, P373