117203-55-1Relevant 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
