N,N‐Dialkylamides of 2‐Hydroxy‐2‐phenyl‐cyclopropan‐1‐carboxylic Acid – Photochemical Synthesis and Determination of the Structure
Irradiation of N,N‐dialkylamides of β‐benzoylpropionic acid 2a, b in ether by n,π*‐excitation leads to the corresponding amides of the hitherto unknown 2‐hydroxy‐2‐phenyl‐cyclo‐propancarboxylic acid 3a, b, 4a, b. The photocyclization yields diastereomeric mixtures E:Z = 2.5–3:1. The determination of the relative configurations is based on the different tendency of dimerization of the E and Z diastereomers.
Photochemistry of Aminoketones. III. Structures and Photochemical Behaviour of β‐Aminovinyl‐phenyl‐ketones in Solvents of Different Polarity
Spectroscopic data of ten selected β‐aminovinyl‐phenyl ketones PhCOCHCR1NR2R3 in polar and nonpolar solutions, respectively, are discussed and the structures assigned. The apparent photochemical inertness of these compounds in alcoholic solution and the irreversible reactions of some enaminoketones in nonpolar medium are explained in terms of relations between the compounds and the polarity of the solvent.
Untersucht werden β‐N,N′‐Dimethyl‐, β‐N,N′‐Diethyl‐, β‐N‐Benzyl‐ und β‐N‐Phenylamino‐ sowie β‐Morpholino‐vinyl‐phenylketon und einige in β‐Stellung am C Methyloder Phenyl‐′substituierte Derivate (IR‐, 1H‐NMR‐ und UV‐Daten).
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