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

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.