The HERON rearrangement in an amino alkoxy formamide
by Arvi Rauk (subsequent pages require MDL's ChemScape
CHIME plugin)
The project involves an attempt to demonstrate the HERON rearrangement
in N-dimethylamino-N-methoxyformamide
(1) and
N-azido-N-methoxyformamide
(2). All calculations were carried out at the B3LYP/6-31G(D)
level of theory with full geometry optimization and harmonic frequency
analysis.
Related Publications
-
A. Rauk and S. A. Glover, a Computational Study of Bisheteroatom Substituted
Amides - Structure and Stereochemistry, J. Org. Chem., 61, 2337-2345
(1996).
-
S. A. Glover, G. Mo, and A. Rauk, HERON Rearrangement of N,N'-Dialkoxy-N,N'-diacylhydrazines,
Tetrahedron, 55, 3413-3426 (1999)
-
S. A. Glover and A. Rauk, Conformational Stereochemistry of the HERON
Amide, N'-methoxy-N-dimethylaminoformamide, J. Org. Chem. 64,
2340-2345 (1999).
-
S. A. Glover, G. Mo, A. Rauk, D. J. Tucker, and P. Turner, Structure,
Conformation, Anomeric Effects, and Rotational Barriers in HERON Amides,
N,N'-Diacyl-N,N'-dialkoxyhydrazines, J. Chem. Soc. Perkin 2, 2053-2058
(1999).