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DOI: 10.1055/s-2005-917082
Synthesis and Photochromic Properties of Cycloalkylidene Fulgides
Publication History
Publication Date:
21 September 2005 (online)
Abstract
A series of cycloalkylidene fulgides have been synthesized using β,γ-unsaturated diesters, instead of the usual α,β-unsaturated diesters. A study of their photochromic properties revealed that an increase in the cycloalkylidene ring size caused a subsequent decrease in the formation of the closed form from the open form.
Key words
photochromic - fulgide - fulgimide - electrocyclic reactions - microwave
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References
The observation of the migration of the double bond was also reported then.
9Compound 10 was obtained in 40% yield and 8 in 9% yield, respectively.
10As determined from crude 1H NMR of the reaction mixture.
11Attempts to obtain the cyclooctylidene succinic diester resulted in the self-condensed product from the cyclooctanone, which was only determined from crude 1H NMR and not isolated. The cyclopentanone used to obtain 11 also tends to afford the self-condensed product quite readily.
12This was to ensure the complete formation of the diacid and to maximize yield. Yields of synthesized fulgides were much lower when this step was omitted.