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2004
Hydrazines
Q 0150
50- 051
Arylation of Diversely Substituted Hydrazines by Tri- and Pentavalent Organobismuth Reagents. — The scope and limitations of the arylation of mono-, di-and trisubstituted hydrazine derivatives by triarylbismuthane and triarylbismuth diacetate
reagents are studied. In the case of mono- and disubstituted hydrazines, pentavalent bismuth compounds are more efficient than trivalent reagents, exemplified by the fast and
highly chemoselective monoarylation of acyl hydrazines at the terminal nitrogen. In
contrast, trisubstituted hydrazines are more efficiently arylated by triarylbismuthanes.
In these cases, a strong influence of steric factors is observed, leading in the appropriate
cases to low yields or complete reaction inhibition. The introduction of two different
aryl moieties into disubstituted hydrazines is demonstrated by a one-pot reaction. —
(TSUBRIK, O.; MAEORG*, U.; SILLARD, R.; RAGNARSSON, U.; Tetrahedron
60 (2004) 38, 8363-8373; Inst. Org. Bioorg. Chem., Tartu Univ., Tartu 51014, Estonia;
Eng.) — Klein
2004
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