Formation, reactions, and NMR spectra of 1,20-cycloatidanes

Formation, reactions, and NMR spectra of 1,20-cycloatidanes

Imines derived from the alkaloid atisine gave N-acetyl 1,20-cycloatidane derivatives when heated with acetic anhydride. Vigorous alkaline hydrolysis cleaved the cyclopropane ring, regenerating the parent imine. The 1 H and 13 C NMR spectra of several 1,20-cyclo derivatives have been assigned and com...

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Veröffentlicht in:Canadian journal of chemistry 1992-05, Vol.70 (5), p.1397-1405
Hauptverfasser: Edwards, Oliver E, Dvornik, Dusan, Kolt, Ralph J, Blackwell, Barbara A
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container_title Canadian journal of chemistry
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creator Edwards, Oliver E
Dvornik, Dusan
Kolt, Ralph J
Blackwell, Barbara A
description Imines derived from the alkaloid atisine gave N-acetyl 1,20-cycloatidane derivatives when heated with acetic anhydride. Vigorous alkaline hydrolysis cleaved the cyclopropane ring, regenerating the parent imine. The 1 H and 13 C NMR spectra of several 1,20-cyclo derivatives have been assigned and compared to those of the parent imines 2 . All of the N-acetyl compounds showed doubling of the majority of the NMR resonances, due to amide rotamers. The effects of the cyclopropane ring current are noted.
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title Formation, reactions, and NMR spectra of 1,20-cycloatidanes
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