CHEMISTRY OF ETHANEDIYL S,S-ACETALS .4. A PROMISING WAY TO CIS-SUBSTITUTED OLEFINS, STEREOSELECTIVELY FROM CARBONYL-COMPOUNDS

被引:5
作者
CAPUTO, R [1 ]
FERRERI, C [1 ]
ISITA, P [1 ]
LONGOBARDO, L [1 ]
MASTROIANNI, D [1 ]
PALUMBO, G [1 ]
机构
[1] NAPLES UNIV,DIPARTIMENTO CHIM ORGAN & BIOL,VIA MEZZOCANNONE 16,I-80134 NAPLES,ITALY
关键词
D O I
10.1080/00397919208019317
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldehydes and methyl ketones readily afford 5,6-dihydro-1,4-dithiins that can be converted by n-butyllithium into their corresponding sulfur stabilized carbanions. Coupling of the latter with alkyl halides leads to species having a cis-configurated, disubstituted double bond tied up by the sulfur-containing ring which is known to be susceptible of selective removal.
引用
收藏
页码:1345 / 1350
页数:6
相关论文
共 7 条
  • [1] CAPUTO R, 1991, SYNTHESIS-STUTTGART, P223
  • [2] THE REACTION OF ETHANEDIYL S,S-ACETALS WITH HALOGENS
    CAPUTO, R
    FERRERI, C
    PALUMBO, G
    CAPOZZI, G
    [J]. TETRAHEDRON, 1986, 42 (08) : 2369 - 2376
  • [3] CHEN CH, 1976, TETRAHEDRON LETT, P25
  • [4] CHENG DCH, 1962, JC T FARADAY SOC, V58, P224
  • [5] NEW SYNTHESIS OF KETONES USING 1-(ALKYLTHIO)VINYLLITHIUM
    OSHIMA, K
    SHIMOJI, K
    TAKAHASH.H
    YAMAMOTO, H
    NOZAKI, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) : 2694 - 2695
  • [6] SAINSBURY M, 1978, RODDS CHEM CARBON 4, V4, P400
  • [7] SELECTIVE MONO-ARYLATION AND MONO-ALKYLATION OF CHLOROPHENYL ALKYL SULFIDES BY NICKEL CATALYZED CROSS-COUPLING WITH GRIGNARD-REAGENTS
    TIECCO, M
    TESTAFERRI, L
    TINGOLI, M
    CHIANELLI, D
    WENKERT, E
    [J]. TETRAHEDRON LETTERS, 1982, 23 (44) : 4629 - 4632