10339. Diisopropyl Azodicarboxylate
Nomenclature
CAS number: 2446-83-5
1,2-Diazenedicarboxylic acid 1,2-bis(1-methylethyl) ester; diisopropyl azodiformate; DIAD. C8H14N2O4; mol wt 202.21.
C 47.52%, H 6.98%, N 13.85%, O 31.65%.
Description and references
Alternative reagent to diethyl azodicarboxylate, q.v., for the Mitsunobu reaction; also applied in other synthetic transformations. Prepn: NL 6408826; GB 1012264 (both 1965 to Wallace & Tiernan Inc.); S. A. Rodkin et al., J. Org. Chem. USSR (Engl. Transl.) 7, 2361 (1971). Synthetic applications: D. L. Hughes, R. A. Reamer, J. Org. Chem. 61, 2967 (1996) DOI PubMed; M. Shi, G.-L. Zhao, Tetrahedron 60, 2083 (2004) DOI; L.-X. Shao, M. Shi, Eur. J. Org. Chem. 2004, 426 DOI; J. Kroutil et al., Synthesis 2004, 446 DOI. Reviews: S. K. Nune, Synlett 2003, 1221-1222 DOI; A. E. Kümmerle, ibid. 2008, 2723-2724 DOI.
