About: The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion

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About: The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Experimental and computational evidence suggests that the cleavage of n-butyl and tert-butyl 3-bromodiazirine-3-carboxylates by sodium n-butoxide in DMF, affording high yields of dibutyl carbonates, may proceed by nucleophilic acyl displacement of the bromodiazirinyl anion, a weakly bound complex of a cyclic carbene c-CN2 (diazirinylidene) and a bromide ion. We explain the formation of substantial amounts of di-n-butoxymethane in the presence of n-butanol by a sequence of O-H insertion and denitrogenation reactions of the putative c-CN2 carbene. This ground-state singlet species is the last undescribed member of the CN2 family of reactive intermediates. It differs from classical N-heterocyclic carbenes by its high ionization potential and electron affinity. Experimental and computational evidence suggests that the cleavage of n-butyl and tert-butyl 3-bromodiazirine-3-carboxylates by sodium n-butoxide in DMF, affording high yields of dibutyl carbonates, may proceed by nucleophilic acyl displacement of the bromodiazirinyl anion, a weakly bound complex of a cyclic carbene c-CN2 (diazirinylidene) and a bromide ion. We explain the formation of substantial amounts of di-n-butoxymethane in the presence of n-butanol by a sequence of O-H insertion and denitrogenation reactions of the putative c-CN2 carbene. This ground-state singlet species is the last undescribed member of the CN2 family of reactive intermediates. It differs from classical N-heterocyclic carbenes by its high ionization potential and electron affinity. (en)
Title	The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion (en)
skos:prefLabel	The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion The Bromodiazirinyl Anion: A Weakly Bound Complex of Diazirinylidene and a Bromide Ion (en)
skos:notation	RIV/60461373:22810/11:43892925!RIV12-MSM-22810___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(LC06070)
http://linked.open...iv/cisloPeriodika	31
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Böhm, Stanislav
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Rektorát
http://linked.open...dnocenehoVysledku	188780
http://linked.open...ai/riv/idVysledku	RIV/60461373:22810/11:43892925
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Diazirines; Nitrogen heterocycles; Diazirinylidene; Carbenoids; Carbenes (en)
http://linked.open.../riv/klicoveSlovo	Carbenes Carbenoids Diazirinylidene Diazirines Nitrogen heterocycles
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[678B83B6CEC1]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	The structure and synthetic applications of transition metal complexes
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	2011
http://linked.open...iv/tvurceVysledku	Böhm, Stanislav Hanzlová, Eva Martinů, Tomáš
http://linked.open...ain/vavai/riv/wos	000296319000011
issn	1434-193X
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201100529
http://localhost/t...ganizacniJednotka	22810

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