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
Permalink