Tetrahedron

Di-p-nitrobenzyl azodicarboxylate (DNAD): an alternative azo-reagent for the Mitsunobu reaction

J Yang, L Dai, X Wang, Y Chen

Index: Yang, Jianhai; Dai, Liyan; Wang, Xiaozhong; Chen, Yingqi Tetrahedron, 2011 , vol. 67, # 7 p. 1456 - 1462

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Citation Number: 11

Abstract

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 ...