77173-43-4Relevant academic research and scientific papers
EVIDENCE FOR SELECTIVE S-ALKYLATION OF AN AMBIDENT ANION OF DICYCLOHEXYLAMMONIUM THIOPHOSPHONATE BY ALKYL HALIDES
Batra, Balwant S.,Purnanand
, p. 169 - 174 (2007/10/02)
Reaction of DCHA salt of O-alkyl phenyl phosphonothioic acids 1a-c with alkyl halides 2a-d gave exclusively S-derivatives; 3e-h (85-93percent) and 3b-d (40-43percent).The cause for poor yields of the methyl analogues is its ability to participate in the methylation of salt 1a and give rise by-product O,S-dimethyl phenyl phosphonothiolate (3a).Awareness of the unusual pathway for the generation of the by-product has opened a new possibility to adopt this strategy for synthesis of enantiomerically pure thiolates. Key words: Chiral phosphonothiolates; dicyclohexylammonium thiophosphonate anion; resolution; stereospecific synthesis; cross methylation; alkyl halides.
