Synthesis and structure of photodegradable 1-(4,5-dimethoxy-2,3-dinitrophenyl)-2-methylpropyl N-butylcarbamate

Abstract

The reaction of 1-(4,5-dimethoxy-2,3-dinitrophenyl)-2-methylpropan-1-ol and butylisocyanate using dibutyltin dilaurate as a catalyst afforded 1-(4,5-dimethoxy-2,3-dinitrophenyl)-2-methylpropyl N-butylcarbamate, C17H25N3O8, which released butylamine upon photoirradiation. Single crystals of the title compound were grown in a 1:1 mixed solution of hexane and ethyl acetate. Two nitro groups and one methoxy group are twisted out of the plane of the aromatic ring in the novel photo-protecting group. Intermolecular hydrogen bonds are observed between N-butylcarbamate moieties parallel to the a axis.

Keywords

• photolabile carbamate
• 2,3-dinitrobenzyl group
• intermolecular hydrogen bonding
• crystal structure