39121-70-5Relevant academic research and scientific papers
Efficient and chemoselective acetalization and thioacetalization of carbonyls and subsequent deprotection using InF3 as a reusable catalyst
Madabhushi, Sridhar,Mallu, Kishore Kumar Reddy,Chinthala, Narsaiah,Beeram, China Ramanaiah,Vangipuram, Venkata Sairam
experimental part, p. 697 - 701 (2012/02/15)
An efficient and chemoselective method for preparation of acetals and dithioacetals of aldehydes and their deprotection under catalysis of InF 3 is described.
Aggregative activation and carbanion chemistry: Complex base deprotonation and directed functionalisation of dithioacetals
Gros, Philippe,Hansen, Philippe,Caubere, Paul
, p. 15147 - 15156 (2007/10/03)
Bis(phenylthio)methane and [1,3]-dithiane were efficiently deprotonated by the NaNH2-Et(OCH2CH2)2-ONa complex base. A marked behaviour difference was observed between the sodium carbanion of [1,3]-dithiane and the corresponding lithio-derivative. A 'radicaloid' mechanism is proposed to explain the results observed.
Organoboranes. 35. Reaction of Alkylthioboronic Esters with Trichloromethyllithium: Preparation of One-Carbon-Extended Carboxylic Acids and Thioacetals from Alkenes via Hydroboration
Brown, Herbert C.,Imai, Toshiro
, p. 892 - 898 (2007/10/02)
Various 2-alkyl-1,3,2-dithiaborolanes, RB(S2C2H4) (1), were converted to the corresponding carboxylic acids, RCO2H (2), by using LiCCl3 in THF, followed by oxidation with alkaline hydrogen peroxide.For R=hexyl, a reaction intermediate is converted by solvent into another compound, C6H13C(S2C2H4)B2 (9a), characterized spectroscopically.The yields of 2 decreased with increasing bulkiness of the alkyl groups R.Although the configuration of R= trans-2-methylcyclopent-1-yl (1k) was retained in the product (>98percent trans), a significant degree of epimerization tookplace for R= exo-norbornyl (1j) during the oxidation (exo : endo = 86 : 14).More uniquely, the intermediates 9 were easily hydrolyzed by heating the reaction mixture with aqueous NaOH to give the corresponding 2-alkyl-1,3-dithiolanes 3.Stereochemical integrity was retained in the products derived from 1j and 1k.Since 1 was prepared by the hydroboration of alkenes, this sequence provides a new method for introducing oxycarbonyl or thioacetal functionality into alkenes in a regioselective manner, and, in the case of 3, also with stereocontrol.
