As compared to oxylyl chloride, is phenyl dichlorophosphate good agent for activate DMSO?
Same if it wirks; do not think it to be a good activating agent (cost and ease to remove).
Look here please to have a greater insight into DMSO activation: http://www.springer.com/cda/content/document/cda_downloaddocument/9780387236070-c2.pdf?SGWID=0-0-45-308299-p55007504
The mechanism should be nearly similar for the one postulated for a typical Swern oxidation.
It is impossible to say ab initio what is good or bed - plethora of DMSO activating agents is used on depends of substrate structure, so use perfect Sławomir Lach citation as guidance.
Please note in this citation (p.118) on Taber modification of the Albright–Onodera oxidation - it is applicable where common activators are failed, ambient temperature for reaction, cheap P2O5 as activator, easy work-up - for what is needed to search anymore?
Like the others said it depends on your molecule and the purpose of the synthesis. If you are looking for scaling up and you want to avoid oxalyl chloride due to tox or P2O5 or similar due to water sensitivity, TsCl or MsCl, could be a good choice. Phenyldichlorophosphate has both bad thigs sensitivity and toxicity, and is economically comparable to other common reagents. If it was my choice I would look for other options unless your yield is quantitative.
I meant that PhOP(=O)Cl2 is not cheap, sorry for mismatched sentence above.
I believe than phenyl dichlorophosphate is cheaper than oxalyl chloride. Nevertheless the choice of Your activator is the function of many variables and it is good to have an overview of opportunities available.
Slawonir, for sure, oxalyl chloride is cheaper than any organic dichlorophosphate. Anyhow I agree with you about the opinion that Hitesh should take into account all factors. Nice link to Swern-like oxidations' review!
See:
Tetrahedron Letters,Vol.29,No.26,pp 3167-3170,1988
PHENYL DICHLOROPHOSPHATE AS AN ACTIVATING AGENT
IN THE PFITZNER-MOFFATT OXIDATION
Hsing-Jang Liu* and James M. Nyangulu
Same mechanism: PhOPCl2 + DMSO to Me2S+OPOCl, and attack on S by the ROH but less side reaction to form Me2SCL2
Bill
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