N, N-Dialkylamide der 2-Hydroxy-2-phenyl-cyclopropan-1-carbonsäure – photochemische Darstellung und Strukturuntersuchung

✍ Scribed by Prof. Dr. H.-G. Henning; Dr. R. Berlinghoff; Dipl.-Chem. A. Mahlow; Dr. H. Köppel; Prof. Dr. K.-D. Schleinitz

• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: English
• Weight: 269 KB
• Volume: 323
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19813230608

✦ Synopsis

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.