Effect of alkyl group size on the mechanism of acid hydrolyses of benzaldehyde acetals

ATN Belarmino, S Froehner, D Zanette…

文献索引：Belarmino, Alexanders T. N.; Froehner, Sandro; Zanette, Dino; Farah, Joao P. S.; Bunton, Clifford A.; Romsted, Laurence S. Journal of Organic Chemistry, 2003 , vol. 68, # 3 p. 706 - 717

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被引用次数: 10

摘要

Hydrolyses of benzaldehyde acetals, PhCH (OR) 2, are specific hydrogen-ion catalyzed when R= methyl, n-butyl, but with secondary and tertiary alkyl derivatives, R= i-propyl, s- butyl, t-butyl, t-amyl, hydrolyses are general-acid catalyzed. The Brønsted α values for both secondary and tertiary alkyl groups are in the range: α= 0.57-0.61. A simple iterative procedure was developed to estimate the individual rate constants for general-acid ...