Über Monornethyl- und Dimethyl-selenanthren

Some Aspects of the Organic Chemistry of Selenium.

“…Selenocyanates (see table 8) The two most important methods for the introduction of the -SeCN group into an organic molecule are represented by equations 1 and 2: Reaction 1 is almost universally applicable for the preparation of compounds in which R is aromatic; the only limitation is that the corresponding diazonium compound be available. The reaction is very similar to the Gatterman modification of the Sandmeyer synthesis of aromatic iodides, and the yields and techniques are quite comparable (16,26,36,37,73,81,185,189). Method 2 is more generally applicable and may be used in any situation where the halogen in the halide is readily displaced by nucleophilic reagents (71,72,88,106,120,124,129,142,175,346,348).…”

“…RSeX + KCN KX + RSeCN Method 3 appears to give good yields, but has few advantages over method 1 or 2, since the prior synthesis of RSeX is required. This method has been employed for the preparation of selenothiocyanates (ArSeSCN) and selenylseleno- (38,189) 4-COOCHa.............................. (196) (36, 189) 3-COOCH¡.............................. cyanates (ArSeSeCN) (110, 300a, 300b) (see table 6). Methods 4 and 5 are of no value synthetically (44, 82).…”

“…4,4'-(OH),................ (191,242) (36, 189,190) 4,4'-(CH3COO)2.......... (191) (7) (l-CioHiSe-),.…”

“…Selenanthrene also by heating a selenoazo compound (189). It is beyond the scope of this review to discuss the multitudinous syntheses which lead to heterocycles containing selenium and another element, usually nitrogen.…”

The Chemistry and Toxicity of Selenium Compounds, with Special Reference to the Selenium Problem.

“…A series of cyclic selenides,-cycloselenopropane, cycloselenobutane, cycloselenopentane, and cycloselenohexane and their derivatives,-were described by Morgan and Burstall (128). Substituted compounds of selenazole (I) (12,37,51,108,107), diazoselenide (II) (100), selenanthrene (III) (39,100,102,103), diphenylene selenide (IV) (39), selendiazole (V) (80), phenoxselenine (VI) (173), selenoxanthene (21), selenoxanthone (56,116,173), selenonaphthene (110,115), phenselenazine, a seleno methylene blue (21), selenothiana (83), 1,4-selenoxane (83), a pelletierine derivative, 3-selen-9-azobicyclo-(3,3,1)-nonane (19), and a spiro compound, 2,6diseleno-4-spiroheptane (4), are known.…”