T. Tsunoda et al., MITSUNOBU TYPE C-N BOND FORMATION WITH ETHYL-3,5,7-HEXAHYDRO-1,2,4,7-TETRAZOCIN-3,8-DIONE (DHTD), A NEW CYCLIC AZODICARBOXAMIDE, Heterocycles, 47(1), 1998, pp. 177-179
The combination of ethyl-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 featur
e of this combination is that it activates the reaction of sec-alcohol
s at room temperature.