1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study
Publication type: Journal Article
Publication date: 2003-06-09
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
A new method was developed for the synthesis of 6-substituted 1,5-diazabicyclo[3.1.0]hexanes and 7-substituted 1,6-diazabicyclo[4.1.0]heptanes by condensation of N-monohalotrimethylene- and N-monohalotetramethylenediamines with carbonyl compounds in the presence of bases. X-ray diffraction studies and quantum-chemical B3LYP/6-31G* calculations demonstrated that the conformations of the resulting bicyclic systems are stabilized by stereoelectronic interactions. As a result, a boat conformation prevails in 1,5-diazabicyclo[3.1.0]hexanes, whereas the energies of chair, half-chair, and boat conformations of 1,6-diazabicyclo[4.1.0]heptanes are equalized.
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Kuznetsov V. V. 1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study // Russian Chemical Bulletin. 2003. Vol. 52. No. 3. pp. 665-673.
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Kuznetsov V. V. 1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study // Russian Chemical Bulletin. 2003. Vol. 52. No. 3. pp. 665-673.
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TY - JOUR
DO - 10.1023/A:1023962907733
UR - https://doi.org/10.1023/A:1023962907733
TI - 1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study
T2 - Russian Chemical Bulletin
AU - Kuznetsov, V. V.
PY - 2003
DA - 2003/06/09
PB - Springer Nature
SP - 665-673
IS - 3
VL - 52
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2003_Kuznetsov,
author = {V. V. Kuznetsov},
title = {1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study},
journal = {Russian Chemical Bulletin},
year = {2003},
volume = {52},
publisher = {Springer Nature},
month = {jun},
url = {https://doi.org/10.1023/A:1023962907733},
number = {3},
pages = {665--673},
doi = {10.1023/A:1023962907733}
}
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Kuznetsov, V. V.. “1,5- Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: A new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study.” Russian Chemical Bulletin, vol. 52, no. 3, Jun. 2003, pp. 665-673. https://doi.org/10.1023/A:1023962907733.
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