108762-93-2Relevant academic research and scientific papers
Electroreduction of Organic Compounds, 19. Formation of Benzoanellated Sulfur Heterocycles by Intramolecular Cathodic Cyclization of Dithiocarboxylic Esters
Gade, Thomas,Streek, Michael,Voss, Juergen
, p. 127 - 142 (2007/10/02)
Cathodic reduction of aryl (3) and benzyl (5) dithiopivaloates and related dithioesters with leaving groups at the benzene ring or a side chain yield the sulfur heterocycles 23, 30 - 32, and 34 depending on the nature of the starting material and the reaction conditions.In the case of the α-oxo-dithioester 22, thioindigo (44) is formed. - The corresponding thioamides 14, 16, and 18 show a strong tendency to reductive dehalogenation but the S,N-heterocycles 38 and 39 are also formed in minor amounts. - The formation of the rearranged products 29 - 32, and 34 isdiscussed in terms of C,S-splitting in the primarily formed radical anion and subsequent C,C-coupling of the fragments and follow-up reactions.Key Words: Dithiopivaloates, S-aryl, S-benzyl / Electroreduction
THIONO AND DITHIOCARBOXYLIC ESTERS WITH ADDITIONAL FUNCTIONAL GROUPS
Voss, Juergen
, p. 129 - 154 (2007/10/02)
Since powerful nucleophiles and reductants or electrophiles are required for the synthesis of thiono and dithio esters, severe difficulties arise if certain other functional groups are present in the precursor.Furthermore, strong interference may occur between a reactive substituent and the thio ester group once they are both present in a molecule. - It is, therefore, necessary - and possible - to choose thoroughly a selective method, if thiono or dithio esters with halogeno, nitro, or oxo substituents as well as bis-thiono and bis-dithio esters are to be prepared.
2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Efficient Acylating Agents for N,N-Dialkylarylamines
Cadamuro, Silvano,Degani, Iacopo,Fochi, Rita,Gatti, Antonella,Regondi, Valeria
, p. 544 - 547 (2007/10/02)
2-Substituted 1,3-benzoxathiolium tetrafluoroborates were used as efficient masked acylating agents for N,N-dialkylarylamines in a two-step reaction.In most of the cases intermediate 2,2-disubstituted 1,3-benzoxathioles were obtained in high yields (about 90percent) and their hydrolysis afforded the corresponding ketones in almost quantitative yields.The new procedure offers the following advantages: (1) the reaction conditions are mild; (2) the acylation proceeds selectively at the para-position as referred to the dialkylamino group; (3) the introduction of a tertiary group is easily accomplished.
