Cyclopropyl-and allyl-substituted arenes in reaction with dinitrogen tetroxide. Effect of substrate oxidation potential on reaction direction

SS Mochalov, RA Gazzaeva, AN Fedotov…

Index: Mochalov; Gazzaeva; Fedotov; Trofimova; Trushkov; Zefirov Russian Journal of Organic Chemistry, 2004 , vol. 40, # 8 p. 1098 - 1112

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Citation Number: 6

Abstract

Abstract A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH 2 Cl 2 and CH 3 CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The correlation provides a possibility to forecast the reaction direction of the mentioned substrates and N 2 O 4. The correlation possesses a general character. It was established for instance that arylcyclo- ...