Abstract
Abstract Whilst studying the use of sulphimides,RN=Sme2, in heterocyclic synthesis we found that N -arylamidinosulphimides can be cleaved photolytically to give imidoylnitrenes which then cyclise to benzimidazoles. When both ortho positions of the N -aryl group are substituted, cyclisation still occurs to give a variety of products derived by rearrangement of the initially formed 3aH-benzimidazole; skeletal rearrangements, [1,5]-, and the rare [1,9]-sigmatropic shifts are proposed. When only one ortho position of the N -aryl group is substituted cyclisation sometimes occurs at this position, as well as at the unsubstituted position, and indeed this unusual process can predominate. Since the proposed 3a H -benzimidazole intermediates could not be isolated, we have undertaken a more general study of their synthesis and of the parent carbocyclic 3a H -indene system; they are still elusive.
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