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Topic: Dess-Martin Periodinane thioacetal deprotection  (Read 1638 times)

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Offline phth

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Dess-Martin Periodinane thioacetal deprotection
« on: September 10, 2014, 06:10:37 PM »
10.1021/ol027518n
OCCCC(C1SCCCS1):rarrow:OCCCCC(=O)
Paper says that it treated the thioacetal with 2 eq and 8 eq of DMP in 9:1 MeCN:DCM anhydrous, then aq workup afforded the product with no observable oxidation of the hydroxyl. 82% yield.


10.1055/s-1995-4114
But other groups observed this in DCM with 1.3 eq DMP; 55% yield:
OCCCCC(C)(C1SCCCS1):rarrow:C(=O)CCCC(C)(C1SCCCS1)

Is this just sterics? Is MeCN quenching DMP to a compound with similar valence to bis(TFA)iodobenzene?

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