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Synthesis, crystal structure and light absorption of vinylogous N,N′-dialkylindigos

✍ Scribed by Lutz Fitjer; Ralf Gerke; Wolfgang Lüttke; Peter Müller; Isabel Usón

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 453 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00906-0

No coin nor oath required. For personal study only.

✦ Synopsis

The base catalyzed N,N'-dialkylation of the vinylogous indigo dye cis-cis-2a proceeds with concomitant isomerization and yields cis-trans-2b,c as minor, and trans-trans-2b,c,d as major products. Upon exposure to light, cis-trans-2b,c isomerizes to trans-trans-2b,c. According to an X-ray analysis, trans-trans-2c and trans-trans-2d are planar. However, due to the different configurations of 2a and 2bd, the light absorption data of 2a-d cannot be used to quantify the inductive effects of the alkyl groups.

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