title: Synthetic utilization of polynitroaromatic compounds. 1. S-derivatization of 1-substituted 2,4,6-trinitrobenzenes with thiols.
abstract: Reactions of 1-R-2,4,6-trinitrobenenes (R = alkyl, protected aldehyde, aminocarbonyl, cyano groups, or isoxazole ring) with thiol salts were investigated. In most cases, these reactions gave a mixture of minor para and major ortho substitution products. Reactions of N,N-disubstituted 2,4,6-trinitrobenzamides with S-,O-, and N-nucleophiles afforded products of substitution of the p-nitro group exclusively. 1-Cyano-2,4,6-trinitrobenzene was found to be the most reactive and the least selective: all three nitro groups can be substituted using an excess of thiol salts. 2-R-4, 6-dinitrobenzamides showed no regioselectivity under similar conditions to yield 1:1 mixtures of para and ortho isomers.
authors: Chemical and Analytical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37831-6197, USA.
authors: S G
authors: SG
authors: Zlotin
authors: P G
authors: PG
authors: Kislitsin
authors: A V
authors: AV
authors: Samet
authors: E A
authors: EA
authors: Serebryakov
authors: L D
authors: LD
authors: Konyushkin
authors: V V
authors: VV
authors: Semenov
authors: A C
authors: AC
authors: Buchanan
authors: A A
authors: AA
authors: Gakh