Citation: Wen Xiang HU, Cheng Ye YUAN, Shu Sen LI. POLAR SUBSTITUENT EFFECTS OF ORGANOPHOSPHORUS ESTERS IN STRUCTURE-REACTIVITY STUDIES[J]. Chinese Chemical Letters, ;1992, 3(8): 579-582. shu

POLAR SUBSTITUENT EFFECTS OF ORGANOPHOSPHORUS ESTERS IN STRUCTURE-REACTIVITY STUDIES

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032

Received Date: 3 March 1992

Fund Project: Project Supported by National Science Foundation of China.

In order to study the polar substituent effect almost with no steric effect in organophosphoruschemistry,a series of 4-substituted-2,6,7-trioxa-1-phosphabicyclo [2.2.2] octane 1-oxides (1) and p-substitutedphenylphosphonates (2) and corresponding mono hexyl esters (3) as model were synthesized.³¹P-NMR chemicalshifts of compounds (1) in methanol and deuterioacetone were determined.The Δδ values reflect 4-sbstituent po-lar effect.The ³¹P-NMR of compounds (2) and (3) and the pKa of compounds (3) were also measured.The results showed that the trend of polar effects of substituents in both carboxylic and organophosphates chemistry are similar.and the change of polar effects in variation with the alkyl groups is not significant.
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