Reaction of 1,8-dehydronaphthalene with carbon disulphide

Abstract

The reaction of carbon disulphide with 1,8-dehydronaphthalene, generated by oxidation of 1-amino-1H-naphtho-[1,8-de]triazine (7), gave naphtho[1,8-bc]thiet (10)(6–8%), naphtho[1,8-de]-1,3-dithiin-2-thione (11)(3–5%), naphtho [1,8-bc]thiophen-2-thione (12)(4–5%), and naphthol [1,8-bc]thiophen-2-one (13)(4–5%). The results can be explained by radical addition of 1,8-dehydronaphthalene to the sulphur atom of carbon disulphide forming a new 1,5-diradical intermediate (8), from which the final products are derived.