Nitrosobenzene: Reagent for the Mitsunobu Esterification Reaction
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43919762" target="_blank" >RIV/60461373:22310/19:43919762 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/19:43919762
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acsomega.8b03551" target="_blank" >https://pubs.acs.org/doi/10.1021/acsomega.8b03551</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsomega.8b03551" target="_blank" >10.1021/acsomega.8b03551</a>
Alternative languages
Result language
angličtina
Original language name
Nitrosobenzene: Reagent for the Mitsunobu Esterification Reaction
Original language description
Nitrosobenzene has been demonstrated to participate in the Mitsunobu reaction in an analogous manner to dialkyl azodicarboxylates. The protocol using nitrosobenzene and triphenylphosphine (1:1) under mild conditions (0 degrees C) provides the ester derivatives of aliphatic and aromatic acids using various alcohols in moderate yield and with good enantioselectivity, giving the desired products predominantly with an inversion of configuration. The proposed mechanism, which is analogous to that observed using dialkyl azodicarboxylates, involves a nitrosobenzene-triphenylphosphine adduct and an alkoxytriphenylphosphonium ion and was supported by density functional theory calculations, P-31 NMR spectroscopy, and experiments conducted with isotopically labeled substrates.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA16-09436S" target="_blank" >GA16-09436S: Photocatalytic and Organocatalytic Mitsunobu Reaction Mediated by Flavin derivatives and Visible Light</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Omega
ISSN
2470-1343
e-ISSN
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Volume of the periodical
4
Issue of the periodical within the volume
3
Country of publishing house
US - UNITED STATES
Number of pages
7
Pages from-to
5012-5018
UT code for WoS article
000462921900053
EID of the result in the Scopus database
2-s2.0-85062785259