76965-78-1Relevant articles and documents
Alcohols as electrophiles: Iron-catalyzed Ritter reaction and alcohol addition to alkynes
Jefferies, Latisha R.,Cook, Silas P.
supporting information, p. 4204 - 4207 (2014/06/09)
A simple, iron-based catalytic system allows for a straightforward method for the synthesis of primary, secondary, and tertiary amides. The system also allows the addition of benzyl alcohols across phenylacetylene to produce substituted phenyl ketones. This transformation improves and expands the substrate scope beyond that previously reported and proceeds under mild reaction conditions, tolerating air and moisture.
Intermolecular ritter-type C-H amination of unactivated sp3 carbons
Michaudel, Quentin,Thevenet, Damien,Baran, Phil S.
supporting information; experimental part, p. 2547 - 2550 (2012/04/04)
Intermolecular Ritter-type C-H amination of unactivated sp3 carbons has been developed. This new reaction proceeds under mild conditions using readily available reagents and an inexpensive source of nitrogen (acetonitrile). A broad scope of substrates can be aminated with this method since many functional groups are tolerated. This reaction also allows for the direct, innate C-H amination of a variety of hydrocarbons such as cyclohexane without the need of prefunctionalization or installation of a directing group.
Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene
Bettinger, Holger F.,Filthaus, Matthias,Bornemann, Holger,Oppel, Iris M.
experimental part, p. 4744 - 4747 (2009/02/06)
(Chemical Equation Presented) C-H insertion: Borylnitrenes, which are generated in situ by photoylsis of azides, convert unactivated alkanes by intermolecular C-H insertion into aminoboranes (see scheme), which in turn can be reacted further to give amines or amides. The boryl group serves two purposes: it converts the nitrene into a highly reactive BN vinylidene analogue, and it is easily cleaved from the product.
Facile conversion of alcohols into N-substituted amides by magnesium hydrogensulfate under heterogeneous conditions
Salehi,Khodaei,Zolfigol,Keyvan
, p. 1947 - 1951 (2007/10/03)
Different classes of alcohols react efficiently with nitriles in the presence of magnesium hydrogensulfate, Mg(HSO4)2, to produce amides in high yields.
Reactions of Thianthrene Cation Radical with Acyclic and Cyclic Alcohols
Shine, Henry J.,Yueh, Wang
, p. 3553 - 3559 (2007/10/02)
Thianthrene cation radical perchlorate (Th(.+)*ClO4(-)) reacted readily with cycloalkanols (C5, C7, C8, and C12), alkan-2-ols (C3, C5, C6, and C8), 3-hexanol, neopentyl alcohol, a number of benzyl alcohols, dl- and (S)-1-phenylethanol, cyclopentyl- and cyclohexylmethanols, the exo- and endo-borneols, and norborneols.Reactions were carried out with an excess of the alcohol in acetonitrile solution containing 2,6-di-tert-butyl-4-methylpyridine.Products were alkenes, ethers, and N-substituted acetamides, depending on the structure of the alcohol.Thianthrene (Th) and its 5-oxide (ThO) were formed in equal amounts.The sum of amounts of products from the alcohol was equal to the amount of ThO.All reactions are interpretable on the basis of the ultimate formation and further reactions of a 5-alkoxythianthreniumyl ion (ROTh(+)).The predominant formation of nortricyclene from the norborneols is striking and is discussed.Swern-Moffatt-type oxidations of the alcohols were not observed.
The Effect of Electrochemically Generated Positive Bromine Species in Acetonitrile on the Cleavage of C-Br and C-Cl Bonds.
Becker, James Y.,Zemach, Dvora
, p. 336 - 340 (2007/10/02)
The fate of bromine formed from C-Br cleavage during the course of anodic oxidation of alkyl bromides in acetonitrile on platinum has been investigated potentiostatically.It is suggested that positive bromine species are formed and they are potentially reactive towards alkyl bromides, yielding similar products to those obtained by direct anodic oxidation of the same bromides.Furthermore, whereas alkyl chlorides do not undergo C-Cl fission by direct anodic oxidation it is shown that positive bromine species are energetically sufficient to break C-Cl bonds, although not very efficiently.We suggest that a possible structure for the complex between acetonitrile and positive bromine species is mainly +Br3- and the mechanism for its formation is discussed.The spectrum of this species found identical to that of Br3- (269 nm) in acetonitrile.
