Superacid and H-Zeolite Mediated Reactions of Benzaldehyde with Aromatic Compounds and Cyclohexane. The Role of Mono- and Dicationic Intermediates Full article
| Journal |
Catalysis Letters
ISSN: 1011-372X , E-ISSN: 1572-879X |
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| Output data | Year: 2004, Volume: 98, Number: 2-3, Pages: 89-94 Pages count : 6 DOI: 10.1007/s10562-004-7919-3 | ||
| Tags | (Super) electrophilic activation, Benzaldehyde, Ionic hydrogenation, Superacids, Zeolites | ||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | University of Southern California | |
| 2 | French National Centre for Scientific Research |
Abstract:
Reactions of benzaldehyde (1) and related compounds–3-pyridinecarboxaldehyde (9) and acetophenone with benzene, chlorobenzene, o-dichlorobenzene and cyclohexane in the presence of superacids or H-form zeolite, HUSY were (re)investigated. In accordance with previous data, 1 condenses with benzene in triflic acid (CF3SO3H) as well as on HUSY to give triphenylmethane. At elevated temperature 1 also reacts with chlorobenzene but is inert towards o-dichlorobenzene. While 1 does not react with cyclohexane in CF3SO3H−SbF5, 9 undergoes readily selective ionic hydrogenation to give 3-pyridilcarbinol (14). In the presence of excess of AlCl3, however, as well as on HUSY, 1 reacts with cyclohexane to produce toluene. The mechanistic aspects of these reactions are discussed. Opposed to earlier, repeatedly cited suggestions that the reactivity of 1 involves, as in case of 9, superelectrophilic diprotonated species, we show that a monocationic intermediate is the best rationale for these results
Cite:
Koltunov K.Y.
, Walspurger S.
, Sommer J.
Superacid and H-Zeolite Mediated Reactions of Benzaldehyde with Aromatic Compounds and Cyclohexane. The Role of Mono- and Dicationic Intermediates
Catalysis Letters. 2004. V.98. N2-3. P.89-94. DOI: 10.1007/s10562-004-7919-3 WOS Scopus РИНЦ ANCAN OpenAlex
Superacid and H-Zeolite Mediated Reactions of Benzaldehyde with Aromatic Compounds and Cyclohexane. The Role of Mono- and Dicationic Intermediates
Catalysis Letters. 2004. V.98. N2-3. P.89-94. DOI: 10.1007/s10562-004-7919-3 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Jul 23, 2004 |
| Accepted: | Jul 27, 2004 |
| Published print: | Nov 1, 2004 |
Identifiers:
| Web of science: | WOS:000224920200005 |
| Scopus: | 2-s2.0-8744261829 |
| Elibrary: | 13467953 |
| Chemical Abstracts: | 2004:938436 |
| Chemical Abstracts (print): | 142:93456 |
| OpenAlex: | W2082708601 |