Target: divinylallene

28 October 2011 - Organic chemistry

divinylallene  Target: 1,1-divinylallene
Publication: Cergol et al., Angewandte 2011 DOI
Extension of: Dendralene chemistry
Key transformation: Grieco elimination
Challenges met: only one of several methods worked
Synthetic steps: a] chloroprene, magnesium, zinc bromide,dibromoethane (Grignard reagent) b] vinylidene chloride, NiCl2(dpppe), THF c] Mg, THF, ZnBr2,formaldehyde, e] 2-nitrophenyl selenocyanate, tributylphosphine f] meta-chloroperbenzoic acid , chloroform , 0°C.
Properties: decomposes above 0°C via multiple Diels-Alder pathways
Conformation: cis-trans
Envisioned application: Rapid synthesis of complex molecules, reacts with three equivalents of maleimide to a complex hexacycle.