Tetrahedron p. 5557 - 5574 (1998)
Update date:2022-08-05
Topics:
Satoh, Tsuyoshi
Takano, Koji
Hiroyuki, Ota
Someya, Hideaki
Matsuda, Kenji
Koyama, Mai
Magnesium alkylidene carbenoids were generated from 1-halovinyl sulfoxides, derived from ketones and aryl halomethyl sulfoxide, through the ligand exchange reaction of sulfoxides with Grignard reagents. The generated magnesium alkylidene carbenoids were found to be stable at -78 °C for over 30 min. The carbenoids reacted with aldehydes to give the adducts in moderate yields; however, they were found to be relatively unreactive to usual electrophiles. The generated magnesium alkylidene carbenoid exists in equilibrium between an α-halo alkenyl Grignard reagent and an alkylidene carbene-magnesium halide complex. Halogen exchange and geometrical isomerization of the alkylidene carbenoids were observed. 1-Chlorovinyl sulfoxides reacted with excess aryl Grignard reagents to give alkenyl Grignard reagents having an aryl group. These Grignard reagents reacted with several electrophiles to give tetra-substituted olefins in moderate to good yields.
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