107389-59-3Relevant articles and documents
Indium(III) chloride as an efficient, convenient catalyst for thioacetalization and its chemoselectivity
Muthusamy, Sengodagounder,Babu, Srinivasarao Arulananda,Gunanathan, Chidambaram
, p. 359 - 362 (2007/10/03)
An efficient method for the preparation of 1,3-dithiolanes from aldehydes and ketones with 1,2-ethanedithiol in the presence of a catalytic amount of anhydrous indium(III) chloride is reported. A mild and highly chemoselective thioacetalization of carbony
Differentation between Carbonyls and Acetals in 1,3-Dithiane and 1,3-Dithiolane Synthesis Catalyzed by Organotin Triflates
Sato, Tsuneo,Otera, Junzo,Nozaki, Hitosi
, p. 4971 - 4978 (2007/10/02)
Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates.In these competition reactions, various types of carbonyls and acetals are differentiated.Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals.The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones.Conversely, an aromatic acetal is more reactive than its parent aldehyde.In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates.However, aromatic acetals react preferentially over aliphatic acetals.Ketones of different types are also differentiated.No such discrimination can be achieved by conventional methods.Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals.Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.
Reactions of 1,3-Dithiolan-2-ylium and 1,3-Dithian-2-ylium Tetrafluoroborates and Ambident 2-Styryl Derivatives
Klaveness, Jo,Rise, Frode,Undheim, Kjell
, p. 373 - 380 (2007/10/02)
The ambident 2-styryl-1,3-dithiolan-2-ylium and 2-styryl-1,3-dithian-2-ylium cations react with preferential carbon-carbon bond formation at the β ethylenic carbon when treated with methylmagnesium iodide.In the lithium aluminium hydride reaction, reduction occurs at either electrophilic carbon center.Methanol and thiophenol react selectively with the β carbon of the side chain.The adduct formation with the heteroatom nucleophiles is readily reversed by acid catalysis.In the absence of the styryl group, the nucleophilic addition is at C-2.Dithioketals of symmetric 1,2-divarbonyl derivatives are readily formed by zinc-induced reductive dimerization of 1,3-dithiolan- and 1,3-dithian-2-ylium salts.
