Ionic and Radical Mechanisms in Olefinic Systems, with Special Reference to Processes of Double-Bond Displacement, Vulcanization and Photogelling

Autor: Ernest Harold Farmer
Rok vydání: 1942
Předmět:
Zdroj: Rubber Chemistry and Technology. 15:774-779
ISSN: 1943-4804
0035-9475
DOI: 10.5254/1.3543163
Popis: The α-methylenic reactions discussed in the preceding two papers recall a series of interesting observations by Baker and Nathan, which indicate that a p-methyl substituent attached to the benzene nucleus can permit electron release to the nucleus in a manner that appears only in lesser degree in higher alkyl groups, and may be absent in some (e.g., Buγ). Thus in p-methylbenzyl bromide, the suggested function of the methyl group (dotted arrows in (I) permits (see PDF for diagram) additional electron release at the C—Br bond, and so facilitates the anionization of the bromine. Baker and Nathan suggest that the electrons of the duplet constituting the C—H bond of the methyl group are less localized than those in a similarly placed C—C bond, and hence that a methyl group attached to the necessary conjugated unsaturated system is capable of electron-release by a mechanism similar to the tautomeric effect
Databáze: OpenAIRE