Journal
TETRAHEDRON
Volume 67, Issue 7, Pages 1456-1462Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.12.036
Keywords
DNAD; Mitsunobu reaction; Azo-reagent; Separation-friendly
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Funding
- Sanhe Pharmachem Co, Ltd
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Di-p-nitrobenzyl azodicarboxylate is prepared in 83.6% yield in two steps as a bright yellow solid, which can be used as an azo-reagent in the Mitsunobu reaction. When a chiral secondary alcohol was used, sufficient configurational inversion of alcohol occurred under Mitsunobu conditions. That the hydrazine produced from DNAD is semisoluble in some solvents such as THF and CH2Cl2 makes it separated easily from the reaction mixture just via filtration. Then the recovered hydrazine compound can be re-exposed to oxidant to produce DNAD. Because DNAD is more stable than DIAD at ambient temperatures and allows easy separation, it is a good alternative azo-reagent for the Mitsunobu reaction. (C) 2010 Elsevier Ltd. All rights reserved.
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