Tetrahedron
Tetrahedron
5 years ago

Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement

Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement
Reaction of (1S*,7R*)-9-oxabicyclo[4.2.1]non-7-en-1-ol (5) with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (6) produced (2R*,4R*)-dimethyl 4-(7-oxooxepan-2-yl)-1,4-dihydropyridazine-3,6-dicarboxylate (11) in a one-pot reaction involving cycloaddition at ambient conditions. The structure of the rearrangement product 11 was determined by X-ray crystallographic analysis. Its formation was discussed based on experimental studies and density functional theory calculations. The driving force of this unusually facile reaction was the stability of the caprolactone product 11 and the extremely exorgenic loss of N2. Structural factors facilitating this rearrangement were also explored employing PCM//M06-2X/6-31G(d, p) calculations.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017307822

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