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

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.