Thermal dealkylation of 2,4-bisalkylamino-6-chloro-s-triazines. Effect of alkyl group structure on dealkylation

Autor:	Milan D. Muškatirović, Živorad D. Tadić
Rok vydání:	1975
Předmět:	Group structure Steric effects chemistry.chemical_classification Olefin fiber chemistry Organic chemistry Alkylation Medicinal chemistry Alkyl
Zdroj:	J. Chem. Soc., Perkin Trans. 2. :1701-1702
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29750001701
Popis:	A number of primary and secondary NN′-dialkyl derivatives of 2,4-diamino-6-chloro-s-triazines were thermally dealkylated at 250 and 280°. The amount of olefin formed increased in the series of primary derivatives (alkyl = Et, Pr, 2-methylpropyl, 2,3-dimethylpropyl) except for the last member. This trend was attributed to the increased hyperconjugative stabilization of the transition state for the reaction which was assumed to proceed viaβ-cis-elimination. The total amount of evolved olefins in the series of secondary derivatives (alkyl = Pri, Bu8, 1,2-dimethylpropyl, 1,3,3-trimethylpropyl) decreases after the second member due to the predominance of steric and statistical factors over the thermodynamic one.
Databáze:	OpenAIRE
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