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Photochemie von Aminoketonen. IV [1]. Synthese von 3-Aryl-pyrrolidinolen-(3) durch Photocyclisierung von β-Amino-propiophenonen (1981)

Henning, H.-G. ; Dietzsch, Th. ; Fuhrmann, J.

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 323 (1981), S. 435-444

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ISSN: 0021-8383

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Photochemistry of Aminoketones. IV. Synthesis of 3-Aryl-pyrrolidinols-(3) via Photocyclization of β-Amino-propiophenonesPhotolysis (λirr ≥ 300 nm) of N-benzyl-N-benzoyl-β-aminopropiophenones 6-9 in abs. ether affords a 47-50% yield of N-benzoyl-pyrrolidinols 12-18. The relative configurations of the diastereomeric 12-18 are determined by 1H-n.m.r. spectroscopy. The different behaviour of the N-acylated 6-9 in contrast to N,N-dialkyl-β-aminopropiophenones is explained by assumption of a dipol-dipol interaction between the keto and the amido carbonylgroups in the n,π*-excited state.

Additional Material: 6 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19813230310

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