Synthesis of Stable Carbamate Phosphorus Ylides by a Four-Component Reaction And Dynamic 1H-Nmr Study of the Energy Barriers for the Rotation around the Carbon–Nitrogen Single Bond and the Carbon–Carbon Double Bond

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Eideh Mofarrah
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Maryam Khosrosharodi

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Elahe Mosaddeg ◽  
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Uwe Schilde
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1971 ◽  
Vol 49 (18) ◽  
pp. 3069-3071 ◽  
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Y. L. Chow ◽  
S. C. Chen ◽  
D. W. L. Chang

The stereochemical course of the photoaddition of nitrosamines to a carbon–carbon double bond was shown to follow a free radical mechanism initiated by aminium radicals. The photoaddition to cyclohexene was highly stereoselective in which the addendum approached in anti-diaxial mode. Similar photoadditions to cis- and trans-2-butenes were less stereoselective, giving mixtures of the erythro- and threo-adducts, owing to the rotation of the carbon-carbon single bond in the intermediate stage.


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