The Journal of organic chemistry

Cyclohexadienone diazeniumdiolates from nitric oxide addition to phenolates

DS Bohle, JA Imonigie

Index: Scott Bohle; Imonigie, Jerome A. Journal of Organic Chemistry, 2000 , vol. 65, # 18 p. 5685 - 5692

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Citation Number: 21

Abstract

Sterically hindered phenols react with nitric oxide under basic condititons to give either cyclohexadienone diazeniumdiolates or oximates. Phenols with 2, 6-di-tert-butyl and 4- methyl (butylated hydroxy toluene, BHT), 4-ethyl, or 4-methoxy methylene substituents yield the corresponding 2, 6-di-tert-butyl-2, 5-cyclohexadienone-4-alkyl-4-diazeniumdiolate salts (4-methyl 1a, 4-ethyl 3a, 4-methoxymethylene 5a). Phenols with 2, 6-di-tert-butyl and 4- ...