INFLUENCE OF PROTONATION ON GATTERMANN-KOCH FORMYLATION RATE OF ALKYLBENZENE IN CF2SO3H-SBF5

被引：21

作者：

TANAKA, M

FUJIWARA, M

ANDO, H

机构：

[1] Osaka National Research Institute, AIST, Osaka, 563, 1-8-31, Midorigaoka, Ikeda

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 07期

关键词：

D O I：

10.1021/jo00112a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of the protonation on Gattermann-Koch formylation rate of alkylbenzenes was studied in CF3SO3H-SbF5. From the kinetic study of m-xylene formylation using various SbF5:m-xylene molar ratios in CF3SO3H, it is revealed that the formylation rate is explained with the equations which take into account the protonation equilibrium of m-xylene, and the apparent formylation rate is decreased by the protonation. The decrease of the apparent formylation rate by the protonation is proportional to the ratio of protonated alkylbenzene to form the a-complex; therefore, the apparent relative formylation rate of alkylbenzenes is not consistent with their relative basicity under strong acidic conditions such as in CF3SO3H-SbF5.

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页码：2106 / 2111

页数：6

相关论文

共 23 条

[1] STUDIES IN TRIFLUOROMETHANESULFONIC ACID .1. PROTONATION OF AROMATIC DERIVATIVES [J].

BAKOSS, HJ ;

RANSON, RJ ;

ROBERTS, RMG ;

SADRI, AR .

TETRAHEDRON, 1982, 38 (05) :623-630

[2] ELECTROPHILIC AROMATIC-SUBSTITUTION .22. NITRATION OF SOME REACTIVE AROMATICS IN METHANESULFONIC ACID, AND THE QUESTION OF POSITIONAL SELECTIVITY IN ENCOUNTER RATE NITRATIONS OF SUBSTITUTED NAPHTHALENES AND 1,2-DIPHENYLETHANES [J].

BARNETT, JW ;

MOODIE, RB ;

SCHOFIELD, K ;

TAYLOR, PG ;

WESTON, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (06) :747-755

[3] NUCLEAR MAGNETIC RESONANCE STUDIES OF PROTONATION OF WEAK BASES IN FLUOROSULPHURIC ACID .3. METHYLBENZENES + ANISOLE [J].

BIRCHALL, T ;

GILLESPIE, RJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1964, 42 (03) :502-&

[4] FORMYLATION AND ACYLATION REACTIONS CATALYZED BY TRIFLUOROMETHANE-SULPHONIC ACID [J].

BOOTH, BL ;

ELFEKKY, TA ;

NOORI, GFM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :181-186

[5] ELECTROPHILIC REACTIONS AT SINGLE BONDS .22. SUPERACID-CATALYZED ELECTROPHILIC FORMYLATION OF ADAMANTANE WITH CARBON-MONOXIDE COMPETING WITH KOCH-HAAF CARBOXYLATION [J].

FAROOQ, O ;

MARCELLI, M ;

PRAKASH, GKS ;

OLAH, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) :864-867

[6]

FUJIYAMA S, 1978, HYDROCARB PROCESS, P147

[7]

Gattermann L., 1897, CHEM BER, V30, P1622

[8]

GRESHAM WF, 1949, Patent No. 2485237

[9] THE BASE STRENGTHS OF AROMATIC HYDROCARBONS RELATIVE TO HYDROFLUORIC ACID IN ANHYDROUS HYDROFLUORIC ACID AS THE SOLVENT [J].

KILPATRICK, M ;

LUBORSKY, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (03) :577-584

[10]

KUDO K, 1986, CHEM EXPRESS, V1, P5