Photoswitchable enediynes: use of cyclopropenone as photocleavable masking group for the enediyne triple bond

10 December 2004

journal article
research article
Published by Royal Society of Chemistry (RSC) in Chemical Communications

No. 5,p. 617-619
https://doi.org/10.1039/b414951c

Abstract

Cyclopropenone 1, 2,3-benzobicyclo[8.1.0]undec-1(10)-en-4-yn-11-one, is a thermally stable compound showing no signs of decomposition after heating at 84 °C for 7 d, UV irradiation of which results in an efficient (Φ₃₀₀ = 0.45) and quantitative formation of benzannelated enediyne 2, which undergoes Bergman cyclization at the above temperature.

Keywords

This publication has 44 references indexed in Scilit:

Bergman cyclopolymerization kinetics of bis- ortho -diynylarenes to polynaphthalene networks. A comparison of calorimetric methods
Polymer, 2000
Photochemical Cycloaromatization of Non-Benzenoid Enediynes
Angewandte Chemie International Edition in English, 1999
Synthesis of polyphenylene derivatives by thermolysis of enediynes and dialkynylaromatic monomers
Tetrahedron, 1997
Synthesis of Nine‐Membered, Masked Enediyne Analogues with DNA Intercalators and Its DNA Cleaving Activities
Angewandte Chemie International Edition in English, 1997
Photochemical analogue of the bergman cycloaromatization reaction
Tetrahedron Letters, 1994
DNA Cleavage, antiviral and cytotoxic reactions photosensitized by simple enediyne compounds
Journal of Photochemistry and Photobiology B: Biology, 1993
General synthesis of cyclopropenones and their acetals
Tetrahedron, 1992
Enediyne Compounds Equipped with Acid‐, Base‐ and Photo‐Sensitive Triggering Devices. Chemical Simulation of the Dynemicin A Reaction Cascade
Angewandte Chemie International Edition in English, 1991
Cyclopropenonchemie, IX. Chemische und photoelektronenspektroskopische Eigenschaften von cyclopropylsubstituierten Cyclopropenonen
European Journal of Inorganic Chemistry, 1977
Das carbenoide Verhalten von Trichlormethyllithium
European Journal of Inorganic Chemistry, 1966