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...

Descripción completa

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
_version_ 1782518112878329856
author Wang, Tongdao
Wang, Long
Daniliuc, Constantin G.
Samigullin, Kamil
Wagner, Matthias
Kehr, Gerald
Erker, Gerhard
author_facet Wang, Tongdao
Wang, Long
Daniliuc, Constantin G.
Samigullin, Kamil
Wagner, Matthias
Kehr, Gerald
Erker, Gerhard
author_sort Wang, Tongdao
collection PubMed
description 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.
format Online
Article
Text
id pubmed-5369402
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-53694022017-04-27 CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template Wang, Tongdao Wang, Long Daniliuc, Constantin G. Samigullin, Kamil Wagner, Matthias Kehr, Gerald Erker, Gerhard Chem Sci Chemistry 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. Royal Society of Chemistry 2017-03-01 2017-01-04 /pmc/articles/PMC5369402/ /pubmed/28451352 http://dx.doi.org/10.1039/c6sc04459j Text en This journal is © The Royal Society of Chemistry 2017 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Wang, Tongdao
Wang, Long
Daniliuc, Constantin G.
Samigullin, Kamil
Wagner, Matthias
Kehr, Gerald
Erker, Gerhard
CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title_full CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title_fullStr CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title_full_unstemmed CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title_short CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template
title_sort co/co and no/no coupling at a hidden frustrated lewis pair template
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369402/
https://www.ncbi.nlm.nih.gov/pubmed/28451352
http://dx.doi.org/10.1039/c6sc04459j
work_keys_str_mv AT wangtongdao cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT wanglong cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT daniliucconstanting cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT samigullinkamil cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT wagnermatthias cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT kehrgerald cocoandnonocouplingatahiddenfrustratedlewispairtemplate
AT erkergerhard cocoandnonocouplingatahiddenfrustratedlewispairtemplate

Ejemplares similares