54305-90-7Relevant articles and documents
New free-radical halogenations of alkanes, catalysed by N-hydroxyphthalimide. Polar and enthalpic effects on the chemo- and regioselectivity
Minisci, Francesco,Porta, Ombretta,Recupero, Francesco,Gambarotti, Cristian,Paganelli, Roberto,Pedulli, Gian Franco,Fontana, Francesca
, p. 1607 - 1609 (2007/10/03)
Reactions of alkanes with different halogenating systems are compared in order to explore the reactivity of phthalimido-N-oxyl radical in hydrogen abstraction; the importance of polar effects is emphasised.
THE LONG-RANGE ACTION OF THE POLAR EFFECT OF SUBSTITUENTS ON THE ABSTRACTION OF HYDROGEN IN FREE-RADICAL CHLORINATION PROCESSES
Aver'yanov, V. A.,Ruban, S. G.,Klykova, M. B.,Golubev, V. E.
, p. 435 - 439 (2007/10/02)
The free-radical chlorination of 1-chloroalkanes between C3 and C6 at 263 deg K was studied under conditions with wide variation in the concentrations of the substrates in benzene.By analysis of the products from chlorination of the pure substrates it was shown that the deactivating effect of the polar substituent does not extend beyond the third carbon atom and is mainly determined by the inductive effect.In the transition to an aromatic solvent the deactivating effect on the substituent extends to the fourth carbon atom.The results are substantiated in terms of a contribution from dipole-dipole interaction between the substituent and the polar form of the transition state to the polar effect of the substituents.
