Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones

[Image: see text] Reaction of α-methylstyrene in the presence of HI gas and methyl p-tolyl ketone selectively resulted in an internal olefinic trimer. We revealed that the ketones with the stabilization of the protonated state were efficient to give the corresponding trimers, whereas the other keton...

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Autores principales: Matsumoto, Shoji, Oseki, Takehisa, Akazome, Motohiro, Otani, Yasuhiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644118/
https://www.ncbi.nlm.nih.gov/pubmed/31458385
http://dx.doi.org/10.1021/acsomega.8b03168
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author Matsumoto, Shoji
Oseki, Takehisa
Akazome, Motohiro
Otani, Yasuhiko
author_facet Matsumoto, Shoji
Oseki, Takehisa
Akazome, Motohiro
Otani, Yasuhiko
author_sort Matsumoto, Shoji
collection PubMed
description [Image: see text] Reaction of α-methylstyrene in the presence of HI gas and methyl p-tolyl ketone selectively resulted in an internal olefinic trimer. We revealed that the ketones with the stabilization of the protonated state were efficient to give the corresponding trimers, whereas the other ketones gave the usual indane compound. From the investigation for the mechanistic path, we found that the trimer is a kinetic product and that indane is a thermodynamic product.
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spelling pubmed-66441182019-08-27 Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones Matsumoto, Shoji Oseki, Takehisa Akazome, Motohiro Otani, Yasuhiko ACS Omega [Image: see text] Reaction of α-methylstyrene in the presence of HI gas and methyl p-tolyl ketone selectively resulted in an internal olefinic trimer. We revealed that the ketones with the stabilization of the protonated state were efficient to give the corresponding trimers, whereas the other ketones gave the usual indane compound. From the investigation for the mechanistic path, we found that the trimer is a kinetic product and that indane is a thermodynamic product. American Chemical Society 2018-12-20 /pmc/articles/PMC6644118/ /pubmed/31458385 http://dx.doi.org/10.1021/acsomega.8b03168 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Matsumoto, Shoji
Oseki, Takehisa
Akazome, Motohiro
Otani, Yasuhiko
Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title_full Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title_fullStr Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title_full_unstemmed Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title_short Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones
title_sort selective formation of internal olefinic trimer of α-methylstyrenes with hi gas and ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644118/
https://www.ncbi.nlm.nih.gov/pubmed/31458385
http://dx.doi.org/10.1021/acsomega.8b03168
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AT osekitakehisa selectiveformationofinternalolefinictrimerofamethylstyreneswithhigasandketones
AT akazomemotohiro selectiveformationofinternalolefinictrimerofamethylstyreneswithhigasandketones
AT otaniyasuhiko selectiveformationofinternalolefinictrimerofamethylstyreneswithhigasandketones

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