80826-97-7Relevant academic research and scientific papers
Novel and highly selective conversion of alcohols and thiols to alkyl nitrites with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu 4NNO2 system
Akhlaghinia, Batool,Pourali, Ali Reza
, p. 1747 - 1749 (2004)
Alkyl nitrites were prepared in good to excellent yields by treatment of alcohols and thiols with triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone/Bu4NNO2 in acetonitrile. This method is highly selective for the conversion of primary alcohols to alkyl nitrites in the presence of secondary and tertiary alcohols and thiols.
Hydrolysis, Nitrosyl Exchange, and Synthesis of Alkyl Nitrites
Doyle, Michael P.,Terpstra, Jan W.,Pickering, Ruth A.,LePoire, Diane M.
, p. 3379 - 3382 (2007/10/02)
Alkyl nitrites undergo relatively slow hydrolysis in phosphate-buffered aqueous media under neutral conditions with small but significant dependence of reactivity on structure.However, rapid nitrosyl exchange with alcohols is observed, and equilibrium constants for this transformation exhibit remarkable correlation with equilibrium constants for nitrosyl exchange of alcohols with nitrosyl chloride and with nitrous acid. tert-Butyl nitrite has the greatest driving force for nitrosyl transfer among the 12 alkyl nitrites examined, and this capability is used for the synthesis of alkyl nitrites derived from steroidal alcohols and of alkyl thionitrites.
