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Title: Stable Carbenes, Nitrenes, Phosphinidenes, and Borylenes: Past and Future

Abstract

The different modes of stabilization for carbenes is briefly discussed in the context of the discovery of their first stable representatives. Due largely to a diversity of stable carbenes available today, their use has spanned across the chemical sciences, including medicinal, and materials applications. Much less is known about the isolobal group 15 cousins of carbenes, namely nitrenes and phosphinidenes, as only one example of each has been isolated. The difficulties associated with their applications are discussed, and possible solutions are presented. As for group 13 element carbenoids, two types are considered: mono(Lewis base)-stabilized borylenes that have been recently isolated, and borylenes, the only carbenoids discussed in this article that have eluded the synthetic skills of investigators. Lastly, this perspective results in a description of potentially attainable targets such as monocoordinated aminocarbanions, aminocarbynes and aminocarbocations, compounds featuring six, five and four valence-electrons, respectively.

Authors:
;
Publication Date:
Research Org.:
Univ. of California, San Diego, La Jolla, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1788111
Alternate Identifier(s):
OSTI ID: 1633004; OSTI ID: 1773895
Grant/Contract Number:  
SC0009376
Resource Type:
Published Article
Journal Name:
Chem
Additional Journal Information:
Journal Name: Chem Journal Volume: 6 Journal Issue: 6; Journal ID: ISSN 2451-9294
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; carbenes; phosphinidenes; borylenes

Citation Formats

Soleilhavoup, Michele, and Bertrand, Guy. Stable Carbenes, Nitrenes, Phosphinidenes, and Borylenes: Past and Future. United States: N. p., 2020. Web. doi:10.1016/j.chempr.2020.04.015.
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Soleilhavoup, Michele, & Bertrand, Guy. Stable Carbenes, Nitrenes, Phosphinidenes, and Borylenes: Past and Future. United States. https://doi.org/10.1016/j.chempr.2020.04.015
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Soleilhavoup, Michele, and Bertrand, Guy. Mon . "Stable Carbenes, Nitrenes, Phosphinidenes, and Borylenes: Past and Future". United States. https://doi.org/10.1016/j.chempr.2020.04.015.
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@article{osti_1788111,
title = {Stable Carbenes, Nitrenes, Phosphinidenes, and Borylenes: Past and Future},
author = {Soleilhavoup, Michele and Bertrand, Guy},
abstractNote = {The different modes of stabilization for carbenes is briefly discussed in the context of the discovery of their first stable representatives. Due largely to a diversity of stable carbenes available today, their use has spanned across the chemical sciences, including medicinal, and materials applications. Much less is known about the isolobal group 15 cousins of carbenes, namely nitrenes and phosphinidenes, as only one example of each has been isolated. The difficulties associated with their applications are discussed, and possible solutions are presented. As for group 13 element carbenoids, two types are considered: mono(Lewis base)-stabilized borylenes that have been recently isolated, and borylenes, the only carbenoids discussed in this article that have eluded the synthetic skills of investigators. Lastly, this perspective results in a description of potentially attainable targets such as monocoordinated aminocarbanions, aminocarbynes and aminocarbocations, compounds featuring six, five and four valence-electrons, respectively.},
doi = {10.1016/j.chempr.2020.04.015},
journal = {Chem},
number = 6,
volume = 6,
place = {United States},
year = {Mon Jun 01 00:00:00 EDT 2020},
month = {Mon Jun 01 00:00:00 EDT 2020}
}
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https://doi.org/10.1016/j.chempr.2020.04.015
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