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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.
  • 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. (en)
Title
  • Evidence for the Cyclic CN2 Carbene in Solution
  • Evidence for the Cyclic CN2 Carbene in Solution (en)
skos:prefLabel
  • Evidence for the Cyclic CN2 Carbene in Solution
  • Evidence for the Cyclic CN2 Carbene in Solution (en)
skos:notation
  • RIV/60461373:22810/14:43898293!RIV15-MSM-22810___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • S
http://linked.open...iv/cisloPeriodika
  • 3
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 15542
http://linked.open...ai/riv/idVysledku
  • RIV/60461373:22810/14:43898293
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • carbenes; diazirines; diazirinylidene; cn2 (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [0292E4E3902F]
http://linked.open...i/riv/nazevZdroje
  • Organic Letters
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 16
http://linked.open...iv/tvurceVysledku
  • Böhm, Stanislav
  • Hanzlová, Eva
  • Martinů, Tomáš
  • Čejka, Jan
  • Navrátil, Rafael
http://linked.open...ain/vavai/riv/wos
  • 000331163900054
issn
  • 1523-7060
number of pages
http://bibframe.org/vocab/doi
  • 10.1021/ol4036243
http://localhost/t...ganizacniJednotka
  • 22810
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