80358-36-7Relevant academic research and scientific papers
PHOSPHORORGANISCHE VERBINDUNGEN 97. Die Diphenylphosphinyl- und die Diphenylthiophosphinylgruppe als selektive Schutzgruppe fuer die Mercaptofunktion. Nucleophile Abloesung der Thioloestergruppe aus Thiophosphin-, Thiophosphon- und Thiophosphorsaeure-S-estern durch nicht solvatisierte...
Horner, L.,Gehring, R.,Lindel, H.
, p. 349 - 356 (2007/10/02)
Diphenylphosphinic acid cyanide and diphenylthiophosphonic acid cyanide react selectively with the mercaptogroup even in presence of primary aminogroups.The thioloesterbond in thiophosphinic, thiophosphonic and thiophosphoric acid S-esters is cleaved under mild conditions by unsolvated fluoride ions F*3H2O (R = C4H9) and CsF> in methylene chloride, chloroform or THF. (C6H5)2P(O)CN and (C6H5)2P(S)CN are therefore protecting group reagents for mercaptans.Diphenylphosphinic acid chloride and diphenylthiophosphinic acid chloride are N-selective in competing reactions using butylamine/butylmercaptan.In contrast to the corresponding S-selective cyanides no selectivity is observed using cysteamine and cysteinmethylester.
