close

Вход

Забыли?

вход по аккаунту

?

код для вставки
2005
Cycloalkylphenyl derivatives
Q 0760
Cyclopropyl- and Allyl-Substituted Arenes in Reaction with Dinitrogen Tetroxide.
of Substrate Oxidation Potential on Reaction Direction. — Application of
08- 094 Effect
relatively simple quantum-chemical calculation of the frontier orbital energy of various
cyclopropylbenzenes, cyclopropylmethylbenzenes and allylbenzenes permits forecasting of the direction of their reactions with N2O4 in less polar solvents like dichloromethane. Thus, the substrates (I), (III) and (VII) possessing more positive calculated
εHOMO values than -9,0 eV (method AM1) mainly undergo nitration of the benzene ring
with the cyclopropyl ring or allyl side chain remaining intact. The mechanism is explained as "electron transfer—recombination of the radical pair" with subsequent
stabilization of the adduct of ion-radical recombination.Substrates possessing more
negative calculated εHOMO values react with cyclopropyl ring cleavage. —
(MOCHALOV, S. S.; GAZZAEVA, R. A.; FEDOTOV, A. N.; TROFIMOVA, E. V.;
TRUSHKOV, I. V.; ZEFIROV, N. S.; Russ. J. Org. Chem. 40 (2004) 8, 1098-1112;
Lomonosov Moscow State Univ., Moscow 119899, Russia; Eng.) — Mischke
Документ
Категория
Без категории
Просмотров
0
Размер файла
25 Кб
Теги
1/--страниц
Пожаловаться на содержимое документа