Photoisomerization as a trigger for Bergman cyclization: synthesis and reactivity of azoenediynes

Kar, Moumita ; Basak, Amit ; Bhattacharjee, Manish (2005) Photoisomerization as a trigger for Bergman cyclization: synthesis and reactivity of azoenediynes Bioorganic & Medicinal Chemistry Letters, 15 (24). pp. 5392-5396. ISSN 0960-894X

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09608...

Related URL: http://dx.doi.org/10.1016/j.bmcl.2005.09.005

Abstract

Cyclic enediynes 1a and 2a containing stable E-azo moiety (azoenediynes) have been synthesized. These compounds upon irradiation with long wavelength UV isomerize to the Z-compounds 1b and 2b, which can be thermally reisomerized to the Z compounds. Reactivity studies toward BC using DSC predictably indicate higher reactivity for the Z-isomers. Our studies may provide a novel way to modulate the reactivity of enediynes under thermal or photochemical conditions.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Photoisomerization; Azoenediyne; Triggering; Bergman Cyclization; Coupling
ID Code:1717
Deposited On:05 Oct 2010 12:05
Last Modified:13 Jan 2011 09:59

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