<div class="csl-bib-body">
<div class="csl-entry">De Pascalis, L., Yau, M.-K., Svatunek, D., Tan, Z., Tekkam, S., Houk, K. N., & Finn, M. G. (2021). The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation. <i>Organic Letters</i>, <i>23</i>(9), 3751–3754. https://doi.org/10.1021/acs.orglett.1c01164</div>
</div>
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dc.identifier.issn
1523-7060
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/139086
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dc.description.abstract
Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels-Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan structure, with substituents at the 2- and 5-positions found to be the most influential and the fragmentation rate to be inversely correlated with electron-withdrawing ability. Density functional theory calculations provided an excellent correlation with the experimentally measured OND rDA rates.
en
dc.language.iso
en
-
dc.publisher
AMER CHEMICAL SOC
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dc.relation.ispartof
Organic Letters
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dc.subject
Biochemistry
en
dc.subject
Physical and Theoretical Chemistry
en
dc.subject
Organic Chemistry
en
dc.subject
Cycloaddition Reaction
en
dc.subject
Molecular Structure
en
dc.subject
Electrons
en
dc.subject
Furans
en
dc.subject
Sulfhydryl Compounds
en
dc.title
The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation
en
dc.type
Artikel
de
dc.type
Article
en
dc.description.startpage
3751
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dc.description.endpage
3754
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dc.type.category
Original Research Article
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tuw.container.volume
23
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tuw.container.issue
9
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tuw.journal.peerreviewed
true
-
tuw.peerreviewed
true
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tuw.researchTopic.id
X1
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tuw.researchTopic.id
C1
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tuw.researchTopic.name
außerhalb der gesamtuniversitären Forschungsschwerpunkte
-
tuw.researchTopic.name
Computational Materials Science
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tuw.researchTopic.value
50
-
tuw.researchTopic.value
50
-
dcterms.isPartOf.title
Organic Letters
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tuw.publisher.doi
10.1021/acs.orglett.1c01164
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dc.identifier.eissn
1523-7052
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dc.description.numberOfPages
4
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tuw.author.orcid
0000-0003-1101-2376
-
tuw.author.orcid
0000-0002-8387-5261
-
tuw.author.orcid
0000-0001-8247-3108
-
wb.sci
true
-
wb.sciencebranch
Chemie
-
wb.sciencebranch.oefos
1040
-
wb.facultyfocus
Chemistry and Technology of Materials
de
wb.facultyfocus
Chemistry and Technology of Materials
en
wb.facultyfocus.faculty
E150
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item.languageiso639-1
en
-
item.openairetype
research article
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item.grantfulltext
restricted
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item.fulltext
no Fulltext
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item.cerifentitytype
Publications
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item.openairecristype
http://purl.org/coar/resource_type/c_2df8fbb1
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crisitem.author.dept
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
-
crisitem.author.dept
University of California, Los Angeles
-
crisitem.author.dept
University of California, Los Angeles
-
crisitem.author.orcid
0000-0003-1101-2376
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
