113391-95-0Relevant academic research and scientific papers
NUCLEOPHILIC CHARACTERISTICS OF NUCLEOFUGIC ANIONS IN THE CLEAVAGE OF EPOXIDES BY PROTIC ACIDS AND NITRONIUM FLUOROBORATE
Zefirov, N. S.,Kirin, V. N.,Yur'eva, N. M.,Zhdankin, V. V.,Kozmin, A. S.
, p. 1264 - 1279 (2007/10/02)
The cleavage of ethylene, propylene, and cyclohexene oxides by protic acids RCOOH (R= CH3, CF3) in the presence of sources of nucleophilic anions (the lithium or tetrabutylammonium salts of perchloric or substituted sulfonic acids) leads to the formation not only of 2-hydroxyalkyl carboxylates but also of significant amounts of 2-hydroxyalkyl perchlorates and sulfonates.In the reactions of the same oxides with nitronium fluoroborate and the above-mentioned salts in methylene chloride 2-perchloryl- and 2-sulfonyloxyalkyl nitrates are formed with high yields; these are the products from opening of the epoxide ring and subsequent combination of the perchlorate and substituted sulfonate ions.The investigated processes extend the range of reactions involving the concurrent combination of nucleofugic anions and can be used as a method for the production of β-hydroxy- and β-nitroxyalkyl perchlorates and sulfonates.
