244056-16-4Relevant articles and documents
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.
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.