55986-20-4Relevant articles and documents
PREPARATION AND REACTION OF N-TOSYL- AND N-ACYLSELENILIMINES
Oae, Shigeru,Fukumura, Mitsuo,Furukawa, Naomichi
, p. 153 - 162 (2007/10/02)
N-Tosyl-Se,Se-diphenylselenilimines (Ia, hydrate state (Ib) of Ia), N-tosyl-Se-methyl-Se-phenylselenilimines (Ic), N-tosyl-Se,Se-dialkylselenilimines (Id-f), N-acyl-Se-aryl-Se-phenyl-selenilimines (IIa-e) and N-acyl-Se,Se-dibenzylselenilimine (IIf) were prepared.The pyrolyses of selenilimines (Ia, d, e, IIa-e) proceeded more readily than those of the corresponding sulfur derivatives.The pyrolyses of N-acyl-Se-aryl-Se-phenylselenilimines gave the corresponding isocyanates in good yields after treatment of the reaction mixture with aniline, together with aryl phenyl selenide.A ki netic study revealed that the rate of pyrolysis of N-benzoyl-Se,Se-diphenylselenilimine (IIa) was 300 times faster than that of the corresponding sulfilimine.The activation enthalpy and entropy were ΔH* = 32.1 kcal/mol and ΔS* = 1.2 e.u. respectively for Ph2Se -> NCOPh.Oxidations of N-tosyl- and N-benzoyl-Se,Se-diphenylselenilimine were carried out with hydrogen peroxide or potassium permanganate to obtain the corresponding selenoxides or selenones, respectively.Hydrolysis of N-tosyl- and N-benzoyl-Se,Se-diphenylselenilimines also took place more readily than that of the corresponding sulfilimines and the selenoxides and the amides were obtained in good yields at room temperature.When N-tosyl-Se,Se-pentamethyleneselenilimine (Ie) was treted with conc. sulfuric acid, a selenurane, Se-hydroxy-Se-(hydroxysulfoxy)selenane (III) was obtained in a high yield.
