CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template

N-Allyltetramethylpiperidine is readily isomerized to the corresponding enamine by treatment with catalytic amounts of B(C(6)F(5))(3). It adds HB(C(6)F(5))(2) at the nucleophilic enamine carbon atom to form a C/B Lewis adduct. This reacts with two molar equivalents of carbon monoxide by selective he...

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Detalles Bibliográficos
Autores principales: Wang, Tongdao, Wang, Long, Daniliuc, Constantin G., Samigullin, Kamil, Wagner, Matthias, Kehr, Gerald, Erker, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369402/
https://www.ncbi.nlm.nih.gov/pubmed/28451352
http://dx.doi.org/10.1039/c6sc04459j
Descripción
Sumario:N-Allyltetramethylpiperidine is readily isomerized to the corresponding enamine by treatment with catalytic amounts of B(C(6)F(5))(3). It adds HB(C(6)F(5))(2) at the nucleophilic enamine carbon atom to form a C/B Lewis adduct. This reacts with two molar equivalents of carbon monoxide by selective head to tail coupling to give a five-membered C(2)O(2)B heterocycle. In contrast the enamine/HB(C(6)F(5))(2) Lewis pair reacts with two molar equiv. of nitric oxide by head to head coupling. This reaction probably proceeds via equilibrium with the corresponding vicinal N/B Lewis pair. Most products were characterized by X-ray diffraction.

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