N,N-Diethylbenzeneselenenamide

Abstract

(R = Et) [57584-86-8] C10H15NSe (MW 228.22) InChI = 1S/C10H15NSe/c1-3-11(4-2)12-10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3 InChIKey = GQTGTQPQZWKTRM-UHFFFAOYSA-N (R = Me) [57584-85-7] C8H11NSe (MW 200.16) InChI = 1S/C8H11NSe/c1-9(2)10-8-6-4-3-5-7-8/h3-7H,1-2H3 InChIKey = KDTBDUMBBGVXNJ-UHFFFAOYSA-N (NR2 = morpholino) [82737-08-4] C10H13NOSe (MW 242.24) InChI = 1S/C10H13NOSe/c1-2-4-10(5-3-1)13-11-6-8-12-9-7-11/h1-5H,6-9H2 InChIKey = QVXXUAVKAJXEHW-UHFFFAOYSA-N (reagent for α-selenenylation of aldehydes2 and β-dicarbonyl compounds;3 areneselenenamides are electrophilic selenium agents for enamines,4 silyl enol ethers,4 and α,β-unsaturated carbonyl compounds,2 and have a more basic character than arenesulfenamides5) Alternate Name: N-phenylseleno-N,N-diethylamine. Physical Data: bp 75 °C/0.1 mmHg. Solubility: sol aprotic solvents; hydrolyzed in water; reacts with alcohols. Form Supplied in: pale yellow oil, often with diphenyl diselenide as impurity. Analysis of Reagent Purity: 1H NMR (CDCl3)6 7.56 (m, 2H) 7.2 (m, 3H) 3.0 (q, J = 7 Hz, 4H) 1.2 (t, J = 7 Hz, 6H). 13C NMR7 131.0, 128.5, 126.9, 53.8, 14.6, 3.0. Preparative Methods: from Benzeneselenenyl Chloride and diethylamine (eq 1).3 Benzeneselenenyl Bromide, formed from Diphenyl Diselenide and Bromine, can also be used.6 The more stable morpholino analog is obtained by the same procedure.4, 9 Optically active areneselenenamides have been prepared from chiral amines.10, 11 Selenenamides are also obtained from N-(trimethylsilyl)dialkylamines (eq 2)7a,12 and used without purification.7a (1) (2) Handling, Storage, and Precautions: can be stored for several weeks below 0 °C in the absence of moisture; like its morpholino analog N-phenylselenomorpholine,8 it can be prepared just before use. Use in a fume hood.