NDLI: Borylnitrenes: electrophilic reactive intermediates with high reactivity towards C

Content Provider	Royal Society of Chemistry (RSC)
Author	Filthaus, Matthias Bettinger, Holger F.
Copyright Year	2010
Abstract	Borylnitrenes (catBN 3a and pinBN 3b; cat = catecholato, pin = pinacolato) are reactive intermediates that show high tendency towards insertion into the C–H bonds of unactivated hydrocarbons. The present article summarizes the matrix isolation investigations that were aimed at identifying, characterizing and investigating the chemical behaviour of 3a by spectroscopic means, and of the experiments in solution and in the gas phase that were performed with 3b. Comparison with the reactivity reported for difluorovinylidene 1a in solid argon indicates that 3a shows by and large similar reactivity, but only after photochemical excitation. The derivative 3b inserts into the C–H bonds of hydrocarbon solvents in high yields and thus allows the formation of primary amines, secondary amines, or amides from “unreactive” hydrocarbons. It can also be used for generation of methylamine or methylamide from methane in the gas phase at room temperature. Remaining challenges in the chemistry of borylnitrenes are briefly summarized.
Starting Page	5477
Ending Page	5482
Page Count	6
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	8
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00107d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Matrix isolation Methane Organic chemistry Methylamine Alkane Methylamide Argon Photochemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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