13154-12-6Relevant articles and documents
Vinylic Organoboranes. 13. A Convenient Stereospecific Synthesis of (Z)-1-Halo-1-alkenes from 1-Alkynes via (E)-1-Alkenylborane Derivatives with Halogens
Brown, Herbert C.,Subrahmanyam, Chitti,Hamaoka, Tsutomu,Ravindran, Nair,Bowman, Donald H.,et al.
, p. 6068 - 6075 (1989)
The reaction of (E)-1-alkenylborane derivatives with bromine under various conditions was investigated, and a simple stereospecific synthesis of (Z)-1-bromo-1-alkenes has been developed.Addition of bromine to (E)-1-alkenyldisiamylborane, derived from the
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
One-pot synthesis of telluroketene acetals and haloketene acetals using sp2 geminated hetero organobismetallic intermediates
Guerrero Jr., Palimécio G.,De Oliveira, Paulo R.,Baroni, Adriano C.M.,Marques, Francisco A.,Labes, Ricardo,Dabdoub, Miguel J.
experimental part, p. 1582 - 1586 (2012/04/10)
A novel one-pot synthesis of 1,1-dihalo-1-alkenes and 1,1-bis(butyltelluro) -1-alkenes was developed from hydrozirconation of alkynylzinc bromide with Cp2Zr(H)Cl and subsequent capture of the Zn/Zr 1,1-heterodimetallo-1- alkene intermediates wi
A convenient preparation of mono- or gem-di-halogenoalkanes from α-sulfonyl carbanions and halogenolithiocarbenoids.
Charreau, Philippe,Julia, Marc,Verpeaux, Jean-Noel
, p. 201 - 210 (2007/10/02)
Various α-sulfonyl carbanions have been shown to react at low temperature with di- or tri-halogenolithiocarbenoids, to give 1-mono- or 1,1-di-halogenoalkanes.Bromocarbenoids gave better results than their chloro-analogues.Reaction of dibromolithiomethane with α-lithiated sulfones gives a high yield of vinylic bromides, the stereochemistry of which is cleanly E.Evidence is presented that the carbenoid itself is responsible for the reaction, and is not first converted into the corresponding carbene.