A highly efficient and selective route to isomeric cyclic diazadienes

ME Scott, Y Bethuel, M Lautens

Index: Scott, Mark E.; Bethuel, Yann; Lautens, Mark Journal of the American Chemical Society, 2007 , vol. 129, # 6 p. 1482 - 1483

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Citation Number: 46

Abstract

Initial optimization studies using 1a and MgI 2 showed that coordinating solvents were most effective (Table 1, entries 1−6), affording the azadiene 3a as the major product in low to modest selectivities and in moderate combined yield. In particular, DME was ideal for this transformation, affording the ring-expanded products after relatively short reaction times in an excellent yield, albeit with modest selectivities (entries 6 and 7). We next focused on modifying the selectivity of the ...