Journal of the Chemical Society. Perkin transactions I p. 413 - 414 (1981)
Update date:2022-08-05
Topics:
Nakayama, Juzo
Dan, Shigeyuki
Hoshino, Masamatsu
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) (6-8percent), naphtho<1,8-de>-1,3-dithiin-2-thione (11) (3-5percent), naphtho<1,8-bc>thiophen-2-thione (12) (4-5percent), and naphtho<1,8-bc>thiophen-2-one (13) (4-5percent).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.
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