244056-16-4Relevant academic research and scientific papers
Conversion of 3-O-substituted 1,2-dibromoalkanes into 2-bromo-1-alkenes by the selective elimination: Its application to total synthesis of 12-oxygenated tremetones
Ohgiya, Tadaaki,Nishiyama, Shigeru
, p. 1084 - 1085 (2004)
2-Bromo-1-alkenes were efficiently synthesized in good yields by the regioselective HBr-elimination reaction of 3-aryloxy- or 3-acyloxy-1,2- dibromoalkanes. Total synthesis of several oxygenated tremetones has been accomplished by using the 2-bromo-1-alkene derivative produced by this elimination reaction.
One-pot method for regioselective bromination and sequential carbon-carbon bond-forming reactions of allylic alcohol derivatives
Kutsumura, Noriki,Matsubara, Yusuke,Niwa, Kentaro,Ito, Ai,Saito, Takao
, p. 3337 - 3346 (2013/06/27)
An efficient one-pot method for the regioselective bromination of allylic alcohol derivatives (two-step reaction sequence) followed by Sonogashira, Negishi, or Suzuki-Miyaura coupling reactions in the same reaction vessel (three-step reaction sequence) ha
TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
experimental part, p. 2377 - 2382 (2011/09/16)
Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.
TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
experimental part, p. 2717 - 2720 (2010/12/25)
Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.
Novel one-pot method for chemoselective bromination and sequential sonogashira coupling
Kutsumura, Noriki,Niwa, Kentaro,Saito, Takao
supporting information; experimental part, p. 3316 - 3319 (2010/10/19)
(Equation Presented). An efficient one-pot method for bromination- elimination of allyl alcohol derivatives and sequential Sonogashira coupling has been developed. A highlight of the method is chemoselective DBU-promoted elimination of vicinal dibromoalka
The synthesis of ethanolamine libraries from olefin scaffolds
Organ,Kaldor,Dixon,Parks,Singh,Lavorato,Isbester,Siegel
, p. 8407 - 8411 (2007/10/03)
A solution-phase, multi-reaction sequence has been developed for the parallel synthesis of ethanolamine libraries. This approach uses 2,3-dibromopropene as a template for the synthesis of a small olefin sub-library, which is then further functionalized to
Neighbouring-group influence on the ring opening of 2-aryloxymethyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
Bakstad, Einar,Olsen, Are S.,Sandberg, Marcel,Sydnes, Leiv K.
, p. 465 - 472 (2007/10/03)
When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.
