96424-16-7Relevant articles and documents
Stereoselective Addition of Carbamates to Unsaturated Systems by Means of Mecury(II) Nitrate. Synthesis of Saturated Nitrogen-containing Heterocycles
Barluenga, J.,Jimenez, C.,Najera, C.,Yus, M.
, p. 1733 - 1736 (2007/10/02)
The aminomercuration of dienes with carbamates and mercury(II) nitrate affords, after in situ demercuration with sodium borohydride, stereoselectively saturated nitrogen-containing heterocycles.Thus, the corresponding amidomercuration-demercuration of 1,4- or 1,5-hexadiene, and diallyl ether gives respectively N-alkoxycarbonyl cis-2,5-dimethylpyrrolidines and trans-3,5-dimethylmorpholines.From 1,5-cyclooctadiene 9-alkoxycarbonyl-9-azabicyclo- and -nonanes (molar ratio ca.1:1) are obtained.By amidomercuration-demercuration of N-allylurethane cis-N,N'-bis(ethoxycarbonyl)-2,5-dimethylpiperazine is obtained.The intermolecular amidomercuration of unsaturated systems results stereochemically opposite to the same aminomercuration process.