<i>o</i>‐nitrovinylbenzaldehyde polymers: Precursors of photosensitive acetals

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<jats:title>Abstract</jats:title><jats:p>2‐Nitro‐3‐vinyl, 2‐nitro‐5‐vinyl, and 4‐nitro‐3‐vinylbenzaldehydes were synthesized starting with the corresponding dimethylnitrobenzenes via brominations of the two methyl groups, subjection of one of the resulting two bromomethyl groups to the Wittig reaction, and further subjection of the remaining one to the Kröhnke reaction.</jats:p><jats:p>An attempt to prepare 2‐nitro‐4‐vinylbenzaldehyde (21) from the 2‐nitro‐4‐vinylaniline (19), synthesized starting with 2‐nitro‐4‐methylaniline following the same vinylation procedure, failed.</jats:p><jats:p>The three nitrovinylbenzaldehydes and 19 were polymerized with AIBN in the conventional manner to afford low molecular weight polymers in low conversions. The polymer of 19 was then converted to the 21 polymer. All nitrobenzaldehyde polymers were converted to acetals with ethylene glycol and 2‐hydroxyethyl salicylate and the latter in benzene solutions were irradiated with UV to afford the <jats:italic>o</jats:italic>‐nitrosobenzoate polymers with half‐cleavages of the alcohol residues.</jats:p>

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