Synthesis and photochemistry of 1,2-naphthoquinonediazide-(2)-n-sulfonic acid derivatives

Add time:07/27/2019    Source:sciencedirect.com

The 1,2-naphthoquinonediazide-(2)-6- and -7-sulfonic acid esters (7c, 7d) have been synthesized for first time starting from the 1-naphthyl-amine-6- and -7-sulfonic acids (1c, 1d), respectively, via Bucherer reaction, nitrosation, reduction, diazotation, sulfochlorination, esterification. The synthesis of the corresponding 8-sulfonic acid ester 73 was not successful by this way. On photolysis the 1,2-naphthoquinonediazide-(2)-6- and -7-sulfonc acid phenyl esters (7c, 7d) form the corresponding (phenoxysulfonyl)-indenecarboxylic acid (10c, 10d) in the same manner like the known 5-sulfonic acid derivative 10b. Different from these isomers, on photolysis of the 4-sulfonic acid ester 7a a photochemically induced ester cleavage occurs additionally (λ <320 nm).

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