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Issue 9, 1972
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Nucleophilic displacement reactions on the new acyl system, 1-bromo-1-(alkyl- or arylthio)-4-aryl-2,3-diazabuta-1,3-diene

Abstract

Reaction of 1,1-dibromo-4-aryl-2,3-diazabuta-1,3-dienes (1,1-dibromoazines) with aliphatic or aromatic thiols yielded products resulting from thiolysis of one or two bromine atoms. The monobromoazine (1-bromo-1-alkylthio-4-aryl-2,3-diazabuta-1,3-diene) is very reactive undergoing replacement of bromine by primary and secondary amines, phenylhydrazine, water, azide ion, alcohols, and phenols to give a variety of novel thiodiaza-systems. The kinetics of displacement by water has been studied in detail in 40% dioxan at 25°. The effect of substituents on the S–Ar ring (ρ=–1·0) is consistent with thioazacarbonium-ion formation as is the observation of a large solvent effect and rate enhancement by the presence of salts other than those containing bromide ion (which causes a rate depression). Direct SN2 displacement of bromide ion is also rendered unlikely by the fact that hydrolysis is slightly slower at high hydroxide ion concentration.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1972, 1050-1056
Article type
Paper

Nucleophilic displacement reactions on the new acyl system, 1-bromo-1-(alkyl- or arylthio)-4-aryl-2,3-diazabuta-1,3-diene

J. Donovan, J. Cronin, F. L. Scott and A. F. Hegarty, J. Chem. Soc., Perkin Trans. 2, 1972, 1050
DOI: 10.1039/P29720001050

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