The Vilsmeier reagent derived from N-formylmorpholine produces chlorothioformates from primary and secondary alkyl xanthates. The major side products are the corresponding alkyl chlorides. Secondary alkyl chlorothioformates give lower yields due to their instability. Treating xanthates with other common chlorinating agents (oxalyl chloride, thionyl chloride) gives only dialkyl thiodicarbonates. Georg Thieme Verlag Stuttgart.
Fikse, Megan A.,Bylund, William E.,Holubowitch, Nicolas E.,Abelt, Christopher J.
p. 4118 - 4120
(2008/03/13)
The chlorination reaction of O-alkyl S-alkyl(aryl) thiophosphoric(-nic) acid derivatives with phosphorus oxychloride
It is reported that a variety of O-alkyl S-alkyl(aryl) thiophosphoric(-nic) acid derivatives 4 can be readily chlorinated with phosphorus oxychloride giving S-alkyl(aryl) thiophosphoro(-no)chloridates 2 and O-alkyl phosphorodichloridates 3.
THE ISOMERIZATION/CHLORINATION OF O,O-DIALKYL PHENYLTHIOPHOSPHONATES WITH PHOSPHORUS OXYCHLORIDE - A NEW CONVENIENT SYNTHESIS OF S-ALKYL PHENYLTHIOPHOSPHONIC ACID DERIVATIVES
A new method for the synthesis of S-alkyl phenylthiophosphonic acid derivatives is reported.The chlorination of O,O-dialkyl phenylthiophosphonates with phosphorus oxychloride proceeds with isomerization to give S-alkyl phenylthiophosphonochloridates, which react further with various nucleophiles in the presence of triethylamine to give the title compounds.Key words: Phosphonothionate; phosphonothiolate; phosphonodithiolate; phosphonamidethiolate; isomerization; chlorination.
A convenient synthesis of S-alkyl O-aryl thiophosphoric acid derivatives
A new convenient synthesis of S-alkyl O-aryl thiophosphoric acid derivatives is reported. The chlorination of O-aryl O,O-dialkyl thiophosphates with phosphorus oxychloride proceeds with isomerization to give S-alkyl O-aryl thiophosphorochloridates, which react further with various nucleophiles in the presence of base to give the title compounds.
Tang,Wu,Zhang
p. 454 - 456
(2007/10/02)
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