61666-77-1Relevant academic research and scientific papers
Enhanced Reactivity of Chelating Ortho Esters and Dithio-Ortho Esters Towards Grignard Reagents
Houghton, Roy P.,Dunlop, Jane E.
, p. 2387 - 2400 (2007/10/02)
2-Alkoxy-1,3-dithianes, 2-alkoxy-1,3-benzdithioles and bis(2-alkoxy-1,3-dioxolanes) react substantially faster with phenylmagnesium bromide and phenylethynylmagnesium bromide when the 2-alkoxy group can act as a chelating system for magnesium(II).
A New Synthetic Application of 1,2-Benzodithiolium Cations: Synthesis of Aldehydes by 1-Carbon Homologation of Carbonyl Compounds
Ceruti, Maurizio,Degani, Iacopo,Fochi, Rita
, p. 79 - 82 (2007/10/02)
Eleven aldehydes (6a-l) were synthesized by 1-carbon homologation of ketones and aldehydes according to the following sequence: Horner-Emmons reaction of 2-(O,O-dimethylphosphonyl)-1,3-benzodithiole (1) and various carbonyl compounds (2) to give benzo-1,4-dithiafulvenes (3); reduction with sodium borohydride and tetrafluoroboric acid-ether complex in dry acetonitrile to 1,3-benzodithioles (5); subsequent hydrolysis of these with mercury(II)oxide and aqueous tetrafluoroboric acid (35percent) in tetrahydrofuran.The procedure is simple, of wide application, and afforded pure aldehydes in good overall yields (55-88percent).
Oxidations with Lead Tetraacetate. IV. Oxidations of 1,3-Benzodithioles
Aromdee, Chantana,Cole, Edward R.,Crank, George
, p. 2499 - 2509 (2007/10/02)
Oxidations of 2,2-dialkyl and spiro with lead tetraacetate gave mainly sulfoxides and disulfoxides.The stereochemistry of these products was elucidated by n.m.r. spectroscopy.Oxidation of 2-methyl-2-aryl derivatives gave sulfoxides as minor products; here the main products were derived from attack on the methyl group forming acetoxy, diacetoxy, formyl and carboxylic acid derivatives and ring cleavage products. 2,2-Diaryl derivatives also formed small amounts of sulfoxides but ring cleavage products were predominant.Monosubstituted benzodithioles were very reactive and produced a variety of oxidation products, mostly unidentified.
