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Communication | Special issue | Vol 47, No. 1, 1998, pp.177-179
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)78
Mitsunobu Type C-N Bond Formation with 4,7-Dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione(DHTD), a New Cyclic Azodicarboxamide

Tetsuto Tsunoda,* Yumi Kawamura, Kaori Uemoto, and Shô Itô*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan


The combination of 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione (DHTD) and tributylphosphine (TBP) was found to mediate successfully C-N bond formation between N-methyltosylamide, a typical N-nucleophile, and several alcohols of different structural types. The unique feature of this combination is that it activates the reaction of sec-alcohols at room temperature.