GENERATION OF MAGNESIUM ALKYLIDENE CARBENOIDS FROM 1-HALOVINYL SULFOXIDES WITH GRIGNARD-REAGENT - THEIR PROPERTY AND SOME SYNTHETIC USES

Authors
SATOH T TAKANO K SOMEYA H MATSUDA K
Citation
T. Satoh et al., GENERATION OF MAGNESIUM ALKYLIDENE CARBENOIDS FROM 1-HALOVINYL SULFOXIDES WITH GRIGNARD-REAGENT - THEIR PROPERTY AND SOME SYNTHETIC USES, Tetrahedron letters, 36(39), 1995, pp. 7097-7100
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
39
Year of publication
1995
Pages
7097 - 7100
Database
ISI
SICI code
0040-4039(1995)36:39<7097:GOMACF>2.0.ZU;2-D
Abstract
The first example of magnesium alkylidene carbenoids is described. 1-H alovinyl sulfoxides 3 (X=F, Cl, Br) were synthesized from ketones and aryl halomethyl sulfoxides in three steps in moderate to good overall yields. Ligand exchange reaction of the sulfoxides of 3 with ethylmagn esium halide in THF at low temperature afforded a magnesium alkylidene carbenoid, which reacted with several electrophiles to give new alkyl idene compounds.