EPR Study on Regioselective Hydrogen Abstraction from p-Substituted Benzaldehydes by“Magic Blue”──The Generation of Perfluoro[(1-propoxyl)ethyl]p-Substituted Benzoyl Nitrooxides andthe Correlation Analyses of TheirαN,αFβValues with Substituent C

Chem. J. Chinese Universities ›› 2005, Vol. 26 ›› Issue (11): 2052.

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EPR Study on Regioselective Hydrogen Abstraction from p-Substituted Benzaldehydes by“Magic Blue”──The Generation of Perfluoro[(1-propoxyl)ethyl]p-Substituted Benzoyl Nitrooxides andthe Correlation Analyses of Theirα_N,α_F^βValues with Substituent C

LI Jin, LIN Zheng-Huan, DOUHong-Yan, ZHAO Cheng-Xue

Department ofChemistry,Shanghai Jiaotong University,Shanghai200240,China

Received:2004-10-08 Online:2005-11-10 Published:2005-11-10

Abstract

Abstract: New“magic blue”reagent containing bis(perfluoroalkyl) nitrooxide [n-C₃F₇OCF(CF₃)]².N(O.)(1) and perfluoronitrosoalkanen-C₃F₇OCF(CF₃) NO_{2 in F113(CCl₂FCClF₂) solution whichwere both generated in the reaction of perfluoro[(2-propoxy)propyonyl] peroxide(n-C₃F₇OCF(CF₃)COO)²with NaNO₂,reacted with a series ofp-substituted benzaldehydes(3)viaregioselective abstraction of the for-myl hydrogen followed with spin trapping ofp-substituted benzoyl radical leading to the stable adducts perflu-oroalkylp-substituted benzoyl nitrooxides4.The correlation analyses ofα_NandαβFwith all kinds of Hammettpolar and spin delocalization substituent constants disclose that the polar factor is the major factor varying spindensity on the nitrogen atom of the nitrooxides though the spin delocalization affects theα_Nvalue slightly.}

Key words: Magic blue, Hydrogen abstraction, p-Substituted benzoyl perfluoroalkyl nitrooxides, Correlationanalysis

CLC Number:

O629

TrendMD:

LI Jin, LIN Zheng-Huan, DOUHong-Yan, ZHAO Cheng-Xue. EPR Study on Regioselective Hydrogen Abstraction from p-Substituted Benzaldehydes by“Magic Blue”──The Generation of Perfluoro[(1-propoxyl)ethyl]p-Substituted Benzoyl Nitrooxides andthe Correlation Analyses of Theirα_N,α_F^βValues with Substituent C[J]. Chem. J. Chinese Universities, 2005, 26(11): 2052.

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EPR Study on Regioselective Hydrogen Abstraction from p-Substituted Benzaldehydes by“Magic Blue”──The Generation of Perfluoro[(1-propoxyl)ethyl]p-Substituted Benzoyl Nitrooxides andthe Correlation Analyses of Theirα_N,α_F^βValues with Substituent C

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