ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Intramolecular Michael addition of 1-acyl-1'-cinnamoylferrocenes. I. Preparation and detection of the isomerism of 2-aryl-3-phenyl[5]ferrocenophane-1,5-dione

P. Elečko

Institut für organische Chemie der Naturwissenschaftlichen Fakultät an der Komenský-Universität, Bratislava 1

Abstract: It has been found that 1-acyl-1'-cinnamoylferrocenes, upon treatment with potassium hydroxide or alumina (pH 6.5 — 7.5) undergo cyclization to form cis- and trans-2,3-disubstituted [5]ferrocenophane-1,5-diones. When allowing to stand over alumina column (pH 6.5 — 7.5), 1-acyl-1'-cinnamoylferrocenes form isomers which upon treatment with potassium hydroxide afford isomers identical with those prepared from 1-acyl-1'-cynnamoylferrocenes with potassium hydroxide directly. LiAlH₄—AlCl₃ reduction of 2,3-disubstituted [5]ferrocenophane-1,5-diones led to 2,3-disubstituted [5]- ferrocenophanes. The formation of isomeric 2,3-disubstituted [5]ferrocenophane derivatives was evidenced by interpretation of infra-red spectra.

Full paper in Portable Document Format: 233a198.pdf (in German)

Chemical Papers 23 (3) 198–211 (1969)