4‐Chloro‐(11b)‐dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐selenide

Abstract

image [863024‐69‐5] C 20 H 12 ClO 2 PSe (MW 429.71) InChI = 1S/C20H12ClO2PSe/c21‐24(25)22‐17‐11‐9‐13‐5‐1‐3‐7‐15(13)19(17)20‐16‐8‐4‐2‐6‐14(16)10‐12‐18(20)23‐24/h1‐12H InChIKey = WZQNXJRLUUZRMH‐UHFFFAOYSA‐N 4‐Chloro‐(11b R )‐dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐selenide image [863024‐82‐2] C 20 H 12 ClO 2 PSe (MW 429.71) InChI = 1S/C20H12ClO2PSe/c21‐24(25)22‐17‐11‐9‐13‐5‐1‐3‐7‐15(13)19(17)20‐16‐8‐4‐2‐6‐14(16)10‐12‐18(20)23‐24/h1‐12H InChIKey = WZQNXJRLUUZRMH‐UHFFFAOYSA‐N 4‐Chloro‐(11b S )‐dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐selenide Physical Data : white solid; mp 240–241 °C. Solubility : stably soluble in aprotic organic solvents. Form Supplied in : not commercially available. Analysis of Reagent Purity : IR (KBr): 3006, 1588, 1509, 1460, 1433, 1355, 1214, 1190, 1157, 1142, 1067, 969, 946, 868, 840, 806, 769, 749, 705, and 652 cm −1 ; 1 H NMR (CDCl 3 ): d 7.22–8.32 (m, 12 H , C 20 H 12 ); 13 C NMR (CDCl 3 ): d 120.4, 121.1, 122.4, 122.6, 126.3, 126.9, 127.0, 127.1, 127.2, 128.7, 131.3, 131.4, 132.0, 132.2, 132.3, 132.5, 146.5, 146.6, 147.8, and 148.0 (Ar); 31 P NMR (CDCl 3 ): d 69.0 ( 1 J P‐Se = 1060.9 Hz); 77 Se NMR (CDCl 3 ): δ −69.2 (d, 1 J P‐Se = 1060.9 Hz). Preparative Method : phosphorus trichloride in toluene solution was treated with triethylamine, ( R ax )‐1,1′‐bi‐2‐naphthol (8.58 g, 30 mmol), and powdered selenium. 1,2 Purification : purified by column chromatography on silica gel with hexane:CH 2 Cl 2 as the eluent. Handling, Storage, and Precautions : the product can be stored for long periods below room temperature under an inert gas atmosphere. In some cases, the product exhibits pink color, which is indicative of the contamination of amorphous selenium, but it can be used for further reaction. Additionally, it gradually hydrolyzes on exposure to moisture in the air. Incompatible with strong acids, strong bases, oxidizing, and reducing agents.