Photochemical transformations. Part XXVIII. Aryl azides as potential photosensitive protecting groups

Abstract

The potential of certain aromatic azides as photosensitive protecting groups has been explored. With alkyl or acyl derivatives of β-(o-azidophenyl)ethyl alcohol photolysis yields indole and the corresponding alcohol or acid. Whereas o-azidobenzyl benzoate is photolysed in protic solvents to give polymers and little of the free acid, derivatives of 5-azido-4-hydroxymethyl-1-methoxynaphthalene are more efficiently photolysed with release of the protected group.