Corrigendum to “Synthesis of heterocyclic compounds using radical reactions and evidence for the formation of spiro radical intermediates”

Ganguly, Ashit K.; Wang, C.H.; Chan, T.M.; Ing, Yao Hain; Buevich, Alexei V.

doi:10.1016/j.tetlet.2004.03.015

Cited by 1 publication

(2 citation statements)

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“…This type of situation misled earlier studies and resulted in the misinterpretation of NOE data and the stereochemistry of dimers 7 and 9. 17,21 It is interesting to note that dimer 9 was found by x-ray crystallographic data to be in anti conformation, which is more concurrent with molecular modeling results. The difference in stability of dimer 9 conformations in the liquid and solid states was ascribed to crystal packing forces.…”

Section: Discussionsupporting

confidence: 65%

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Structure determination and conformation analysis of symmetrical dimers

Buevich¹,

Chan²,

Wang

et al. 2004

Magnetic Reson in Chemistry

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Conformational and stereochemical analysis of six new symmetrical dimers was performed using proton-proton vicinal coupling measured from (1)H NMR and (13)C satellites of (1)H NMR signals, natural abundance (13)C-edited nuclear overhauser effect (NOE) experiments, comprehensive NOE analysis and molecular modeling. The (13)C satellite analysis and (13)C-edited NOE experiments were carried out to extract spectral information between equivalent protons. Molecular modeling was applied for estimations of three-dimensional parameters of the studied dimers, which were subsequently used to generate a set of theoretical NOE for each possible conformation. The J-coupling, (13)C-edited NOE and quantitative NOE analyses showed the predominance of gauche conformation for three dimers, whereas a mixture of gauche and anti conformations (45:55) for three other dimers was established by quantitative NOE analysis. X-ray crystallographic study confirmed the stereochemistry of one of the dimers and revealed a discrepancy in conformation stability between liquid and solid states.

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Section: Discussionsupporting

confidence: 65%

“…Thus, both insufficient data regarding conformational distribution and the inaccuracy of molecular modeling led to the reverse assignment of 7 and 9 stereochemistry, 17 and therefore a correction has been made. 21 The new assignment of dimer 9 was also confirmed by single-crystal x-ray analysis (Fig. 7).…”

Section: Structure Determination Of Dimers 7 9 and 11mentioning

confidence: 57%