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Ketenimine from cyanoisopropyl radicals

Cyanoisopropyl radicals (15) undergo unsymmetrical C-N coupling in preference to C-C coupling.11 1 The preferential formation of the ketenimine is a reflection of the importance of polar and steric influences.1"1 However, the ketenimine is itself thermally unstable and a source of 15, thus the predominant isolated product is often from C-C coupling. [Pg.257]

Preferential C-N coupling is also observed for oligomeric radicals (Scheme 5.9).117 A ketenimine (21) is the major product from the reaction of the "dimeric" MAN radical 18 with cyanoisopropyl radicals (15). Only one of the two possible ketcnimincs was observed a result which is attributed to the thermal lability of ketenimine 19. If this explanation is correct then, although C-N coupling may... [Pg.257]

In the decomposition of AIBN, besides the formation of the products (tetramethyl succinonitrile (TMSN), isobutyronitrile (IBN) and MAN) from the normal Carbon-Carbon reaction of the cyanoisopropyl radicals, a ketenimine (5) from a Carbon-Nitrogen reaction also occurs. This arises because one of a pair of cyanoisopropyl radicals can tautomerize to a keteniminyl radical which subsequently reacts with the second cyanoisopropyl radical to form the ketenimine. This reaction is thermally reversible and the ultimate products would be TMSN, IBN and any polymerized MAN. [Pg.18]


See also in sourсe #XX -- [ Pg.76 , Pg.116 , Pg.257 ]




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