1623-07-0Relevant articles and documents
Kirby,Varvoglis
, p. 406 (1967)
Dissociative reactions of benzonorbornadienes with tetrazines: Scope of leaving groups and mechanistic insights
Xu,Galindo-Murillo,Cheatham,Franzini
, p. 9855 - 9865 (2017/12/12)
Bioorthogonal dissociative reactions boast diverse potential applications in chemical biology and drug delivery. The reaction of benzonorbornadienes with tetrazines to release amines from carbamate leaving groups was recently introduced as a bioorthogonal bond-cleavage reaction. The present study aimed at investigating the scope of leaving groups that are compatible with benzonorbornadienes. Synthesis of several benzonorbornadienes with different releasable groups is reported, and the reaction of these molecules with tetrazine was found to be rapid and afforded high release yields. The tetrazine-induced release of molecules proceeds in a cascade of steps including inverse-electron demand cycloaddition and cycloreversion reactions that form unstable isoindoles/isobenzofuran intermediates and spontaneously eliminate a leaving group of interest. In the case of oxygen-bridged BNBDs at room temperature, we observed the formation of an unproductive byproduct.
One-pot synthesis of organophosphate monoesters from alcohols
Lira, Lucas M.,Vasilev, Dimitar,Pilli, Ronaldo A.,Wessjohann, Ludger A.
, p. 1690 - 1692 (2013/04/10)
A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile.
