Ring opening and closing in heterocyclic compounds.1H nuclear magnetic resonance studies on the reaction between 6-nitrobenzothiazole and methoxide ion in dimethyl sulphoxide–methanol
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 14,p. 1472-1474
- https://doi.org/10.1039/p29750001472
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.Keywords
This publication has 0 references indexed in Scilit: