Issue 3, 2004

Synthesis of cycloalkynesvia photochemical decarboxylation of ω-phthalimidoalkynoates

Abstract

The photodecarboxylation reactions of ω-phthalimidoalkynoates have been studied and the influence of the geometrically restricted acetylene linker on the photocyclization efficiency investigated. Less flexible starting materials give solely CO2H/H-exchange products in good yields. In contrast, derivatives with appropriate chain lengths give the corresponding macrocycles in fair to moderate isolated yields. Furthermore, photodecarboxylative addition of alkynoates to N-methylphthalimide gives hydroxyphthalimidines in acceptable yields.

Graphical abstract: Synthesis of cycloalkynes via photochemical decarboxylation of ω-phthalimidoalkynoates

Supplementary files

Article information

Article type
Paper
Submitted
02 Oct 2003
Accepted
18 Dec 2003
First published
20 Jan 2004

Photochem. Photobiol. Sci., 2004,3, 311-316

Synthesis of cycloalkynes via photochemical decarboxylation of ω-phthalimidoalkynoates

D. J. Yoo, E. Y. Kim, M. Oelgemöller and S. C. Shim, Photochem. Photobiol. Sci., 2004, 3, 311 DOI: 10.1039/B312263H

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