Evidence for the Cyclic CN2 Carbene in Solution

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F14%3A43898293" target="_blank" >RIV/60461373:22310/14:43898293 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/14:43898293
Result on the web
<a href="http://pubs.acs.org/doi/abs/10.1021/ol4036243" target="_blank" >http://pubs.acs.org/doi/abs/10.1021/ol4036243</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/ol4036243" target="_blank" >10.1021/ol4036243</a>

Result language
angličtina
Original language name
Evidence for the Cyclic CN2 Carbene in Solution
Original language description
Diazirinylidene (c-CN2) is formally the simplest of the N-heterocyclic carbenes. The intermediacy of this elusive species in the fragmentation of butyl 3-bromodiazirine-3-carboxylate (1a) with pent-4-en-1-ols and their sodium alkoxides in DMF is supported by the formation of 2-oxabicyclo[4.1.0]heptanes and dipentenoxymethanes. These products result from an intramolecular [2 + 1] cycloaddition and O-H insertion, respectively, of pentenoxymethylenes suggested to originate from the reaction of the electrophilic c-CN2 with an alkoxide ion. The reaction of 1a with primary or secondary amines in methanol affords the corresponding 3-bromodiazirine-3-carboxamides.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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