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Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones

✍ Scribed by Maria J. Milewska; Maria Gdaniec; Tadeusz Poloński

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
381 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

Several optically active substituted 3-azabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues have been synthesized, and their circular dichroism spectra studied. The crystal structure of thiolactam la showed that the bicyclic skeleton of the title compounds assumes a sofa-like geometry. It is postulated that the cyclopropyl moiety and amide or thioamide group constitute an inherently chiral chromophore, helicity of which determines the Cotton effect sign corresponding to the n-rr* electronic transition. The weak rr-rr* Cotton effect of thiolactams shows opposite sign to that observed for the lowest energy excitation. (~) 1997 Elsevier Science Ltd

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