Abstract
The reversible interaction between 6-nitrobenzothiazole and methoxide ion in DMSO or DMSO–MeOH mixtures leads to the open anion 2-methoxymethyleneamino-5-nitrobenzenethiolate (III), via a Meisenheimer-like adduct. Addition of CH3I or Br2–pyridine in CCI4 to the reaction mixtures yields 2-methoxymethyleneamino-5-nitrophenyl methyl sulphide or bis-(2-methoxymethyleneamino-5-nitrophenyl) disulphide respectively. 1H N.m.r. studies show that in DMSO–MeOH rapid addition of MeOH to the NC double bond of (III) occurs.
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