83152-87-8Relevant articles and documents
RING OPENING OF CYCLOHEXENE EPOXIDE WITH TRIMETHYLSILYL CYANIDE
Spessard, Gary O.,Ritter, Allen R.,Johnson, Dawn M.,Montgomery, Anne M.
, p. 655 - 656 (1983)
Contrary to its reaction with epoxides in the presence of aluminum catalysts, trimethylsilyl cyanide reacts with cyclohexene epoxide to give 2-hydroxycyclohexyl isonitrile in the presence of ZnCl2.
Reaction of Cyanotrimethylsilane with Oxiranes. Effect of Catalysts or Mediators on Regioselectivity and Ambident Character
Imi, Katsuharu,Yanagihara, Naoto,Utimoto, Kiitiro
, p. 1013 - 1016 (2007/10/02)
Reaction of cyanotrimethylsilane with oxiranes under the catalytic action of Lewis acids Pd(CN)2, SnCl2, or Me3Ga affords 2-trimethylsiloxy isocyanides by regio- and stereoselective attack of isocyanide on the more substituted carbon.The reaction mediated by aluminium alkoxides gives predominantly 3-trimethylsiloxy nitriles by the selective attack of cyanide on the less substituted carbon.
The Synthesis and Some Reactions of Thiazolidine-2-selones
Cambie, Richard C.,Rutledge, Peter S.,Tan, Vivien Y. Y.,Woodgate, Paul D.
, p. 3655 - 3694 (2007/10/02)
As a route to thiazolidine-2-selones or the tautomeric 2-thiazolines, the reactions of trans-1-iodo-2-isothiocyanatocyclohexane with selenium nucleophiles have been investigated.Sodium hydrogenselenide gives a mixture of the 2-selone (2) and 2-thione (3) while lithium selenide gives mainly the 2-thione (3).With these reagents trans-1-iodo-2-isocyanatocyclohexane gives the corresponding selenazolidin-2-one (5).Treatment of 2-lithiobenzothiazole with N-phenylselenophthalimide or diphenyl diselenide gives 2-phenylselenobenzothiazole, while reaction of the sodium salt of selenobenzothiazole with alkyl or allyl halides affords high yields of 2-alkylseleno- and 2-allylselenobenzothiazoles, respectively.Treatment of 2-decylselenobenzothiazole with either hydrogen peroxide or m-chloroperbenzoic acid leads to low yields of the Pummerer rearrangement product (40). 2-Prop-2'-enylselenobenzothiazole can be used as a transfer reagent in palladium-catalysed allylation of diethyl malonate.Alternative routes to vic-iodoselenocyanates have been investigated.
