NNNS chemistry blog


Home
All blogs
May 2012
April 2012
March 2012
February 2012
January 2012
December 2011
November 2011
October 2011
September 2011
August 2011
July 2011
June 2011
May 2011
April 2011
March 2011
February 2011
January 2011
December 2010
November 2010
October 2010
September 2010
August 2010
July 2010
June 2010
May 2010
Synth. methods III
Synthetic methods
March 2010
Named Reactions
Archive
Internet
Admin
Contact
RSS feed

NNNS software
© Van der Lingen 2012
 
Previous | Next |All

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.