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Carbon‐13 Nuclear Magnetic Resonance Spectroscopic Analyses of 3‐Aryl‐3‐hydroxyl‐2,2,4,4‐tetramethylcyclobutanones and Related Compounds

 

作者: Shaw‐Tao Lin,   Wen‐Chung Lin,   Yuen‐Han Yeh,  

 

期刊: Journal of the Chinese Chemical Society  (WILEY Available online 2000)
卷期: Volume 47, issue 1  

页码: 275-278

 

ISSN:0009-4536

 

年代: 2000

 

DOI:10.1002/jccs.200000034

 

出版商: WILEY‐VCH Verlag

 

关键词: 13C NMR;Cyclobutanones;SCS;Pentadiones;Field effect;Resonance‐induced effect

 

数据来源: WILEY

 

摘要:

AbstractA series of 2‐aryl‐2‐hydroxy‐1,1,3,3‐tetramethyl‐5,8‐dioxaspiro[3.4]octanes (1), 3‐aryl‐3‐hydyoxyl‐2,2,4,4‐tetyramethylcyclobutanones (2), and l‐aryl‐2,2,4‐trimethyl‐1,3‐pentadiones (3) were studied using13C NMR analyses. The chemical shifts of C‐c are dependent on the substituent groups on the phenyl ring for compounds1(ρ =‐0.966, R2= 0.987) and2(ρ = −1.378, R2= 0.998). The chemical shifts of C‐a follow a similar trend (ρ =−0.926, R2= 0.989). In the case of compounds3, C‐c yielded the opposite trend with very poor correlation coefficiency (ρ = 1.22, R2= 0.179). This result reveals the field effect of a polar bond and resonance‐induced changes in pi el

 

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