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81 5-AminoFischer’s base was condensed with the diacid chlorides of glutaric, pimelic, and azelaic acids to give in 70–92% yields the bis-amides, which upon reaction with 5-nitrosalicylaldehyde gave 70–88% of the bis-spiropyrans (72, n = 3,5,7). The alternative route, reaction of the acid chlorides with 5'-amino-6nitroBIPS, is impractical because of the difficulty of obtaining this BIPS. The bisBIPS exhibit strong photochromism. 4. Substitution in Spiropyrans The spiropyrans can be brominated with N-bromosuccinimide (NBS) in chloroform to give various substitution patterns that are dependent upon the nature of the two halves of the molecule.

In a third approach, one can prepare a spiropyran and then introduce new substituents, or transform substituents already present. Scheme 2 14 Robert C. Bertelson The first method is perhaps the most common, and is exemplified by the condensation shown in Scheme 3 of a 2-alkyl heterocyclic quaternary salt or the corresponding methylene base with a 2-hydroxy unsaturated aldehyde grouping (which usually is part of an aromatic ring, as in salicylaldehyde). These intermediates have given a broad assortment of spiropyran classes.

These were used as intermediates for cyanine dyes; their conversion to spiropyrans was not recorded. , in the 5,6-position) were prepared from 6-amino-1,2,3,3-tetramethylindoline by reaction with acetoacetic ester to give an 86% yield of the 1,2,3,3,5-pentamethyl-2,3,7,8tetrahydro-1 H ,8H -pyrrolo[3,2-g]quinolin-7-one (32), converted to the corresponding 7-chloroquinoline (33) in 80% yield with phosphorus oxychloride. Both the chloroquinoline and its precursor quinolone gave the corresponding Fischer’s base upon oxidation with mercuric acetate.

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Advanced chemical oxidation treatment of dye wastewater and remediation of chlorinated aromatic


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